chemicallytechFine Chemical TechnologiesТонкие химические технологии2410-65932686-7575MIREA – Russian Technological University (RTU MIREA).10.32362/2410-6593-2022-17-4-275-297chemicallytech-1857Research ArticleCHEMISTRY AND TECHNOLOGY OF ORGANIC SUBSTANCESХИМИЯ И ТЕХНОЛОГИЯ ОРГАНИЧЕСКИХ ВЕЩЕСТВFeatures of heterogeneous catalytic transformations of strained carbocyclic compounds of the norbornene seriesОсобенности гетерогенно-каталитических превращений напряженных карбоциклических соединений норборненового рядаhttps://orcid.org/0000-0003-4842-3283ДураковС. А.DurakovS. A.

Дураков Сергей Алексеевич, к.х.н., доцент кафедры физической химии им. Я.К. Сыркина

119571, Москва, пр-т Вернадского, д. 86

Scopus Author ID 57194217518

ResearcherID AAS-6578-2020

SPIN-код РИНЦ 9420-3916

Sergey A. Durakov, Cand. Sci. (Chem.), Associate Professor, Department of Physical Chemistry

86, Vernadskogo pr., Moscow, 119571

Scopus Author ID 57194217518

ResearcherID AAS-6578-2020

RSCI SPIN-code 9420-3916

s.a.durakov@mail.ruhttps://orcid.org/0000-0003-2194-4935КолобовА. А.KolobovA. A.

Колобов Алексей Андреевич, студент кафедры физической химии им. Я.К. Сыркина

119571, Москва, пр-т Вернадского, д. 86

Alexey A. Kolobov, Student, Department of Physical Chemistry

86, Vernadskogo pr., Moscow, 119571

a.a.kolobov@bk.ruhttps://orcid.org/0000-0001-6559-5648ФлидВ. Р.FlidV. R.

Виталий Рафаилович Флид, д.х.н., профессор, заведующий кафедрой физической химии им. Я.К. Сыркина

119571, Москва, пр-т Вернадского, д. 86

Scopus Author ID 6602997346

ResearcherID H-1781-2017

SPIN-код РИНЦ 8790-3380

Vitaly R. Flid, Dr. Sci. (Chem.), Professor, Head of the Department of Physical Chemistry

86, Vernadskogo pr., Moscow, 119571

Scopus Author ID 6602997346

ResearcherID H-1781-2017

RSCI SPIN-code 8790-3380

vitaly-flid@yandex.ruМИРЭА - Российский технологический университет (Институт тонких химических технологий им. М.В. Ломоносова)РоссияMIREA - Russian Technological University (M.V. Lomonosov Institute of Fine Chemical Technologies)Russian Federation202230092022174275297Copyright © Durakov S.A., Kolobov A.A., Flid V.R., 20222022Дураков С.А., Колобов А.А., Флид В.Р.Durakov S.A., Kolobov A.A., Flid V.R.Данная работа распространяется под лицензией Creative Commons Attribution 4.0.This work is licensed under a Creative Commons Attribution 4.0 License.https://www.finechem-mirea.ru/jour/article/view/1857

Objectives. Catalytic processes involving norbornene (NBN) and norbornadiene (NBD) offer exceptional opportunities for the synthesis of a wide range of hard-to-reach polycyclic hydrocarbons. The problems of selectivity and manufacturability of these reactions are fundamentally important for their practical implementation. The aim of this review is to summarize the latest advances in the field of designing heterogeneous catalysts for the preparation and transformation of promising NBN- and NBD-derivatives with the maintenance of a strained carbocyclic framework in isomerization and dimerization reactions of these compounds.Results. Various strategies for the selection of catalysts and prospects for the development of heterogeneous catalysis for syntheses based on NBN and NBD derivatives were considered. The possibility of selective cyclic dimerization and isomerization of NBN and NBD was shown. The factors that affect the direction of the reactions and make it possible to maintain the strained norbornane structure were discussed.Conclusions. An analysis of the current state of this problem showed that at present, the technological parameters of the conversion of NBD and NBN derivatives with the participation of heterogeneous catalysts are significantly inferior to homogeneous systems. In order to improve the productivity of these processes and design catalyst regeneration, further investigations are required. However, some progress in these areas has already been made. In a number of processes, it is possible not only to maintain the strained carbocyclic framework, but also to establish ways to control regio- and stereo-selectivity. In some cases, the use of heterogeneous catalysts allows the process to be direct into a completely new path, which has no analogues for homogeneous systems.

Цели. Каталитические процессы с участием норборнена (НБН) и норборнадиена (НБД) открывают исключительные возможности для синтеза широкого круга труднодоступных полициклических углеводородов. Проблемы избирательности и технологичности этих реакций принципиально важны для их практической реализации. Целью обзора является обобщение последних достижений в области создания гетерогенных катализаторов для получения и превращений перспективных НБН- и НБД-производных с сохранением напряженного карбоциклического каркаса в реакциях их изомеризации и димеризации.Результаты. Рассмотрены различные стратегии подбора катализаторов и перспективы развития гетерогенного катализа для синтезов на основе НБН и НБД производных. Показана возможность селективного проведения циклической димеризации и изомеризации НБН и НБД. Обсуждены факторы, влияющие на направление реакций и позволяющие сохранять напряженную норборнановую структуру.Выводы. Анализ современного состояния данной проблемы показывает, что в настоящее время технологические показатели процессов превращения НБД и НБН-производных с участием гетерогенных катализаторов существенно уступают гомогенным системам. Их оптимизация, увеличение производительности и регенерация катализатора требует дальнейшего изучения и совершенствования. Тем не менее, на данном этапе достигнуты определенные успехи. В ряде процессов удается не только сохранить напряженный карбоциклический каркас, но и установить пути управления регио- и стерео-селективностью. В некоторых случаях применение гетерогенных катализаторов позволяет направить процесс в совершенно новое русло, не имеющее аналогов для гомогенных систем.

норборненнорборнадиенгетерогенный катализдимеризацияизомеризацияпереходные металлыцеолитынапряженные карбоциклические соединенияnorbornenenorbornadieneheterogeneous catalysisdimerizationisomerizationtransition metalszeolitesstrained carbocyclic compoundsReferencesФлид В.Р., Грингольц М.Л., Шамсиев Р.С., Финкельштейн Е.Ш. Норборнен, норборнадиен и их производные – перспективные полупродукты для органического синтеза и получения полимерных материалов. Успехи химии. 218;87(12):1169–1205.Flid V.R., Gringolts M.L., Shamsiev R.S., Finkelshtein E.S. Norbornene, norbornadiene and their derivatives: promising semi-products for organic synthesis and production of polymeric materials. Russ. Chem. Rev. 2018;87(12):1169–1205. https://doi.org/10.1070/RCR4834Gusevskaya E.V., Jiménez-Pinto J., Börner A. Hydroformylation in the Realm of Scents. ChemCatChem. 2014;6(2):382–411. https://doi.org/10.1002/cctc.201300474Gusevskaya E.V., Jiménez-Pinto J., Börner A. Hydroformylation in the Realm of Scents. ChemCatChem. 2014;6(2):382–411. https://doi.org/10.1002/cctc.201300474González A.G., Barrera J.B. Chemistry and Sources of Mono- and Bicyclic Sesquiterpenes from Ferula Species. In: Herz W., Kirby G.W., Moore R.E., Steglich W., Tamm C. (Eds.). Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products. Vienna: Springer; 1995. V. 64. P. 1–92. https://doi.org/10.1007/978-3-7091-9337-2_1González A.G., Barrera J.B. Chemistry and Sources of Mono- and Bicyclic Sesquiterpenes from Ferula Species. In: Herz W., Kirby G.W., Moore R.E., Steglich W., Tamm C. (Eds.). Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products. Vienna: Springer; 1995. V. 64. P. 1–92. https://doi.org/10.1007/978-3-7091-9337-2_1Mane J., Clinet I., Muratore A., Clinet J.-C., Chanot J.-J. New aldehydes with norbornane structures, their preparation and use in perfume making: Pat. EP2112132A1. Publ. 28.10.2009.Mane J., Clinet I., Muratore A., Clinet J.-C., Chanot J.-J. New aldehydes with norbornane structures, their preparation and use in perfume making: Pat. EP2112132A1. Publ. 28.10.2009.Buchbauer G., Stappen I., Pretterklieber C., Wolschann P. Structure–activity relationships of sandalwood odorants: synthesis and odor of tricyclo β-santalol. Eur. J. Med. Chem. 2004;39(12):1039–1046. https://doi.org/10.1016/j.ejmech.2004.09.014Buchbauer G., Stappen I., Pretterklieber C., Wolschann P. Structure–activity relationships of sandalwood odorants: synthesis and odor of tricyclo β-santalol. Eur. J. Med. Chem. 2004;39(12):1039–1046. https://doi.org/10.1016/j.ejmech.2004.09.014Monti H., Corriol C., Bertrand M. Synthese stereoselective DU (±)-β-santalol. Tetrahedron Lett. 1982;23(52):5539–5540. https://doi.org/10.1016/S0040-4039(00)85888-8Monti H., Corriol C., Bertrand M. Synthese stereoselective DU (±)-β-santalol. Tetrahedron Lett. 1982;23(52):5539–5540. https://doi.org/10.1016/S0040-4039(00)85888-8Corey E.J., Shibasaki M., Nicolaoua K.C., Malmsten C.L., Samuelsson B. Simple, stereocontrolled total synthesis of a biologically active analog of the prostaglandin endoperoxides (PGH2, PGG2). Tetrahedron Lett. 1976;(10):737–740. https://doi.org/10.1016/s0040-4039(00)77938-xCorey E.J., Shibasaki M., Nicolaoua K.C., Malmsten C.L., Samuelsson B. Simple, stereocontrolled total synthesis of a biologically active analog of the prostaglandin endoperoxides (PGH2, PGG2). Tetrahedron Lett. 1976;(10):737–740. https://doi.org/10.1016/s0040-4039(00)77938-xLee M., Ikeda I., Kawabe T., Mori S., Kanematsu K. Enantioselective Total Synthesis of cis-Trikentrin B. J. Org. Chem. 1996;61(10):3406–3416. https://doi.org/10.1021/jo951767qLee M., Ikeda I., Kawabe T., Mori S., Kanematsu K. Enantioselective Total Synthesis of cis-Trikentrin B. J. Org. Chem. 1996;61(10):3406–3416. https://doi.org/10.1021/jo951767qHajiyeva G.E. Biologically Active Norbornene Derivatives: Synthesis of Bicyclo[2.2.1]heptene Mannich Bases. Chemistry for Sustainable Development. 2021;29(4):391–410. https://doi.org/10.15372/CSD2021317Hajiyeva G.E. Biologically Active Norbornene Derivatives: Synthesis of Bicyclo[2.2.1]heptene Mannich Bases. Chemistry for Sustainable Development. 2021;29(4):391–410. https://doi.org/10.15372/CSD2021317Songstad D.D., Duncan D.R., Widholm J.M. Effect of l-aminocyclopropane-l-carboxylic acid, silver nitrate, and norbornadiene on plant regeneration from maize callus cultures. Plant Cell Reports. 1988;7(4):262–265. https://doi.org/10.1007/bf00272538Songstad D.D., Duncan D.R., Widholm J.M. Effect of l-aminocyclopropane-l-carboxylic acid, silver nitrate, and norbornadiene on plant regeneration from maize callus cultures. Plant Cell Reports. 1988;7(4):262–265. https://doi.org/10.1007/bf00272538Brar M.S., Moore M.J., Al-Khayri J.M., Morelock T.E., Anderson E.J. Ethylene inhibitors promote in vitro regeneration of cowpea (Vigna Unguiculata L.). In Vitro Cell. Dev. Biol.-Plant. 1999;35(3):222–225. https://doi.org/10.1007/s11627-999-0082-1Brar M.S., Moore M.J., Al-Khayri J.M., Morelock T.E., Anderson E.J. Ethylene inhibitors promote in vitro regeneration of cowpea (Vigna Unguiculata L.). In Vitro Cell. Dev. Biol.-Plant. 1999;35(3):222–225. https:// doi.org/10.1007/s11627-999-0082-1Brooks G.T. Chlorinated Insecticides: Technology and Application. V. 1. CRC Press; 2017. 249 p. https://doi.org/10.1201/9781315150390Brooks G.T. Chlorinated Insecticides: Technology and Application. V. 1. CRC Press; 2017. 249 p. https://doi.org/10.1201/9781315150390Tanaka R., Kamei I., Cai Z., Nakayama Y., Shiono T. Ethylene-Propylene Copolymerization Behavior of ansa-Dimethylsilylene(fluorenyl)(amido)dimetyltitanium Complex: Application to Ethylene-Propylene-Diene or Ethylene-Propylene-Norbornene Terpolymers. J. Polym. Sci. Part A: Polym. Chem. 2015;53(5):685–691. https://doi.org/10.1002/pola.27494Tanaka R., Kamei I., Cai Z., Nakayama Y., Shiono T. Ethylene-Propylene Copolymerization Behavior of ansa-Dimethylsilylene(fluorenyl)(amido)dimetyltitanium Complex: Application to Ethylene-Propylene-Diene or Ethylene-Propylene-Norbornene Terpolymers. J. Polym. Sci. Part A: Polym. Chem. 2015;53(5):685–691. https://doi.org/10.1002/pola.27494Касьян Л.И. Стереохимические аспекты эпоксидирования замещенных норборненов и сопровождающие эту реакцию внутримолекулярные превращения. Успехи химии. 1998;67(4):299–316.Kasyan L.I. Epoxidation of substituted norbornenes. Stereochemical aspects and accompanying intramolecular transformations. Russ. Chem. Rev. 1998;67(4):263–278. https://doi.org/10.1070/RC1998v067n04ABEH000355Финкельштейн Е.Ш., Бермешев М.В., Грингольц М.Л., Старанникова Л.Э., Ямпольский Ю.П. Замещенные полинорборнены – перспективные материалы для газоразделительных мембран. Успехи химии. 2011;80(4):362–383.Finkelshtein E.Sh., et al. Substituted polynorbornenes as promising materials for gas separation membranes. Russ. Chem. Rev. 2011;80(4):341–361. https://doi.org/10.1070/RC2011v080n04ABEH004203Fonseca L.R., Silva Sa J.L., Carvalho V.P., Lima-Neto B.S. Cross-link in norbornadiene-based polymers from ring-opening metathesis polymerization with pyrrolidinebased Ru complex. Polym. Bull. 2018;75(8):3705–3721. https://doi.org/10.1007/s00289-017-2236-3Fonseca L.R., Silva Sa J.L., Carvalho V.P., Lima-Neto B.S. Cross-link in norbornadiene-based polymers from ring-opening metathesis polymerization with pyrrolidinebased Ru complex. Polym. Bull. 2018;75(8):3705–3721. https://doi.org/10.1007/s00289-017-2236-3Ono Y., Kawashima N., Kudo H., Nishikubo T., Nagai T. Synthesis of new photoresponsive polyesters containing norbornadiene moieties by the ring-opening copolymerization of donor-acceptor norbornadiene dicarboxylic acid anhydride with donor-acceptor norbornadiene dicarboxylic acid monoglycidyl ester derivatives. J. Polym. Sci. Part A: Polym.Chem. 2005;43(19):4412–4421. https://doi.org/10.1002/pola.20911Ono Y., Kawashima N., Kudo H., Nishikubo T., Nagai T. Synthesis of new photoresponsive polyesters containing norbornadiene moieties by the ring-opening copolymerization of donor-acceptor norbornadiene dicarboxylic acid anhydride with donor-acceptor norbornadiene dicarboxylic acid monoglycidyl ester derivatives. J. Polym. Sci. Part A: Polym.Chem. 2005;43(19):4412–4421. https://doi.org/10.1002/pola.20911Tsubata A., Uchiyama T., Kameyama A., Nishikubo T. Synthesis of Poly(ester-amide)s Containing Norbornadiene (NBD) Residues by the Polyaddition of NBD Dicarboxylic Acid Derivatives with Bis(epoxide)s and Their Photochemical Properties. Macromolecules. 1997;30(19):5649–5654. https://doi.org/10.1021/ma970431aTsubata A., Uchiyama T., Kameyama A., Nishikubo T. Synthesis of Poly(ester-amide)s Containing Norbornadiene (NBD) Residues by the Polyaddition of NBD Dicarboxylic Acid Derivatives with Bis(epoxide)s and Their Photochemical Properties. Macromolecules. 1997;30(19):5649–5654. https://doi.org/10.1021/ma970431aYalcinkaya E.E., Balcan M., Güler C. Synthesis, characterization and dielectric properties of polynorbornadiene-clay nanocomposites by ROMP using intercalated Ruthenium catalyst. Mater. Chem. Phys. 2013;143(1):380–386. https://doi.org/10.1016/j.matchemphys.2013.09.014Yalcinkaya E.E., Balcan M., Güler C. Synthesis, characterization and dielectric properties of polynorbornadiene-clay nanocomposites by ROMP using intercalated Ruthenium catalyst. Mater. Chem. Phys. 2013;143(1):380–386. https://doi.org/10.1016/j.matchemphys.2013.09.014Alentiev D.A., Bermeshev M.V. Design and Synthesis of Porous Organic Polymeric Materials from Norbornene Derivatives. Polym. Rev. 2022;62(2):400–437. https://doi.org/10.1080/15583724.2021.1933026Alentiev D.A., Bermeshev M.V. Design and Synthesis of Porous Organic Polymeric Materials from Norbornene Derivatives. Polym. Rev. 2022;62(2):400–437. https://doi.org/10.1080/15583724.2021.1933026Alentiev D.A., Dzhaparidze D.M., Gavrilova N.N., Shantarovich V.P., Kiseleva E.V., Topchiy M.A., et al. Microporous Materials Based on Norbornadiene-Based Cross-Linked Polymers. Polymers. 2018;10(12):1382. https://doi.org/10.3390/polym10121382Alentiev D.A., Dzhaparidze D.M., Gavrilova N.N., Shantarovich V.P., Kiseleva E.V., Topchiy M.A., et al. Microporous Materials Based on Norbornadiene-Based Cross-Linked Polymers. Polymers. 2018;10(12):1382. https://doi.org/10.3390/polym10121382Aladyshev A.M., Klyamkina A.N., Nedorezova P.M., Kiseleva E.V. Synthesis of Ethylene-Propylene-Diene Terpolymers and Their Heterophase Compositions with Polypropylene in the Presence of Metallocene Catalytic Systems. Russ. J. Phys. Chem. B. 2020;14(4):691–696. https://doi.org/10.1134/S1990793120040028Aladyshev A.M., Klyamkina A.N., Nedorezova P.M., Kiseleva E.V. Synthesis of Ethylene-Propylene-Diene Terpolymers and Their Heterophase Compositions with Polypropylene in the Presence of Metallocene Catalytic Systems. Russ. J. Phys. Chem. B. 2020;14(4):691–696. https://doi.org/10.1134/S1990793120040028Sveinbjornsson B.R., Weitekamp R.A., Miyake G.M., Xia Y., Atwater H.A., Grubbs R.H. Rapid self-assembly of brush block copolymers to photonic crystals. Proceedings of the National Academy of Sciences (PNAS). 2012;109(36):14332–14336. https://doi.org/10.1073/pnas.1213055109Sveinbjornsson B.R., Weitekamp R.A., Miyake G.M., Xia Y., Atwater H.A., Grubbs R.H. Rapid self-assembly of brush block copolymers to photonic crystals. Proceedings of the National Academy of Sciences (PNAS). 2012;109(36):14332–14336. https://doi.org/10.1073/pnas.1213055109Grubbs R.H., Miyake G.M., Weitekamp R., Piunova V. Chiral polymers for the self-assembly of photonic crystals: Pat. US9575212-B2. Publ. 21.02.2017.Grubbs R.H., Miyake G.M., Weitekamp R., Piunova V. Chiral polymers for the self-assembly of photonic crystals: Pat. US9575212-B2. Publ. 21.02.2017.Wang Z., Chan C.L.C., Zhao T.H., Parker R.M., Vignolini S. Recent Advances in Block Copolymer Self-Assembly for the Fabrication of Photonic Films and Pigments. Adv. Optical Mater. 2021;9(21):2100519. https://doi.org/10.1002/adom.202100519Wang Z., Chan C.L.C., Zhao T.H., Parker R.M., Vignolini S. Recent Advances in Block Copolymer Self-Assembly for the Fabrication of Photonic Films and Pigments. Adv. Optical Mater. 2021;9(21):2100519. https://doi.org/10.1002/adom.202100519Kudo H., Yamamoto M., Nishikubo T., Moriya O. Novel Materials for Large Change in Refractive Index: Synthesis and Photochemical Reaction of the Ladderlike Poly(silsesquioxane) Containing Norbornadiene, Azobenzene, and Anthracene Groups in the Side Chains. Macromolecules. 2006;39(5):1759–1765. https://doi.org/10.1021/ma052147mKudo H., Yamamoto M., Nishikubo T., Moriya O. Novel Materials for Large Change in Refractive Index: Synthesis and Photochemical Reaction of the Ladderlike Poly(silsesquioxane) Containing Norbornadiene, Azobenzene, and Anthracene Groups in the Side Chains. Macromolecules. 2006;39(5):1759–1765. https://doi.org/10.1021/ma052147mKato Y., Muta H., Takahashi S., Horie K., Nagai T. Large Photoinduced Refractive Index Change of Polymer Films Containing and Bearing Norbornadiene Groups and Its Application to Submicron-Scale Refractive-Index Patterning. Polym J. 2001;33(11):868–873. https://doi.org/10.1295/polymj.33.868Kato Y., Muta H., Takahashi S., Horie K., Nagai T. Large Photoinduced Refractive Index Change of Polymer Films Containing and Bearing Norbornadiene Groups and Its Application to Submicron-Scale Refractive-Index Patterning. Polym J. 2001;33(11):868–873. https://doi.org/10.1295/polymj.33.868Philippopoulos C., Economou D., Economou C., Marangozis J. Norbornadiene-quadricyclane system in the photochemical conversion and storage of solar energy. Ind. Eng. Chem. Prod. Res. Dev. 1983;22(4):627–633. https://doi.org/10.1021/i300012a021Philippopoulos C., Economou D., Economou C., Marangozis J. Norbornadiene-quadricyclane system in the photochemical conversion and storage of solar energy. Ind. Eng. Chem. Prod. Res. Dev. 1983;22(4):627–633. https://doi.org/10.1021/i300012a021Брень В.А., Дубоносов А.Д., Минкин В.И., Черноиванов В.А. Норборнадиен–квадрициклан — эффективная молекулярная система аккумулирования солнечной энергии. Успехи химии. 1991;60(5):913–948.Bren’ V.A., et al. Norbornadiene–quadricyclane — an effective molecular system for the storage of solar energy. Russ. Chem. Rev. 1991;60(5):451–469. https://doi.org/10.1070/RC1991v060n05ABEH001088Дубоносов А.Д., Брень В.А., Черноиванов В.А. Норборнадиен-квадрициклан – абиотическая система для аккумулирования солнечной энергии. Успехи химии. 2002;71(11):1040–1050.Dubonosov A.D., et al. Norbornadiene–quadricyclane as an abiotic system for the storage of solar energy. Russ. Chem. Rev. 2002;71(11):917–927. https://doi.org/10.1070/RC2002v-071n11ABEH000745Jevric M., Petersen A.U., Manso M., Singh S.K., Wang Z., Dreos A., et al. Norbornadiene-Based Photoswitches with Exceptional Combination of Solar Spectrum Match and Long-Term Energy Storage. Chem. Eur. J. 2018;24(49):12767–12772. https://doi.org/10.1002/chem.201802932Jevric M., Petersen A.U., Manso M., Singh S.K., Wang Z., Dreos A., et al. Norbornadiene-Based Photoswitches with Exceptional Combination of Solar Spectrum Match and Long-Term Energy Storage. Chem. Eur. J. 2018;24(49):12767–12772. https://doi.org/10.1002/chem.201802932Manso M., Petersen A.U., Wang Z., Erhart P., Nielsen M.B., Moth-Poulsen K. Molecular solar thermal energy storage in photoswitch oligomers increases energy densities and storage times. Nat. Commun. 2018;9(1):1945. https://doi.org/10.1038/s41467-018-04230-8Manso M., Petersen A.U., Wang Z., Erhart P., Nielsen M.B., Moth-Poulsen K. Molecular solar thermal energy storage in photoswitch oligomers increases energy densities and storage times. Nat. Commun. 2018;9(1):1945. https://doi.org/10.1038/s41467-018-04230-8Wang Z., Roffey A., Losantos R., Lennartson A., Jevric M., Petersen A.U., et al. Macroscopic heat release in a molecular solar thermal energy storage system. Energy Environ. Sci. 2019;12(1):187–193. https://doi.org/10.1039/C8EE01011KWang Z., Roffey A., Losantos R., Lennartson A., Jevric M., Petersen A.U., et al. Macroscopic heat release in a molecular solar thermal energy storage system. Energy Environ. Sci. 2019;12(1):187–193. https://doi.org/10.1039/C8EE01011KDreos A., Wang Z., Udmark J., Ström A., Erhart P., Börjesson K., et al. Liquid Norbornadiene Photoswitches for Solar Energy Storage. Adv. Energy Mater. 2018;8(18):1703401. https://doi.org/10.1002/aenm.201703401Dreos A., Wang Z., Udmark J., Ström A., Erhart P., Börjesson K., et al. Liquid Norbornadiene Photoswitches for Solar Energy Storage. Adv. Energy Mater. 2018;8(18):1703401. https://doi.org/10.1002/aenm.201703401Большаков Г.Ф. Химия и технология компонентов жидкого ракетного топлива. Л: Химия; 1983. 318 с.Bol’shakov G.F. Khimiya i tekhnologiya komponentov zhidkogo raketnogo topliva (Chemistry and technology of liquid propellant components). Leningrad: Khimiya; 1983. 318 p. (in Russ.).Norton R.V., Fisher D.H., Graham G.M., Frank P.J. Method for preparing high density liquid hydrocarbon fuels: Pat. US-4355194-A. Publ. 19.10.1982.Norton R.V., Fisher D.H., Graham G.M., Frank P.J. Method for preparing high density liquid hydrocarbon fuels: Pat. US-4355194-A. Publ. 19.10.1982.Burns L.D. Motor fuel: Pat. US-4387257-A. Publ. 07.06.1983.Burns L.D. Motor fuel: Pat. US-4387257-A. Publ. 07.06.1983.Lun P., Qiang D., Xiutianfeng E., Genkuo N., Xiangwen Z., Jijun Z. Synthesis Chemistry of High- Density Fuels for Aviation and Aerospace Propulsion. Prog. Chem. 2015;27(11):1531–1541. https://doi.org/10.7536/PC150531Lun P., Qiang D., Xiutianfeng E., Genkuo N., Xiangwen Z., Jijun Z. Synthesis Chemistry of High- Density Fuels for Aviation and Aerospace Propulsion. Prog. Chem. 2015;27(11):1531–1541. https://doi.org/10.7536/PC150531Kim J., Shim B., Lee G., Han J., Jeon J.-K. Synthesis of High-energy-density Fuel through Dimerization of Bicyclo[2.2.1]hepta-2,5-diene over Co/HY Catalyst. Appl. Chem. Eng. 2018;29(2):185–190. https://doi.org/10.14478/ace.2017.1116Kim J., Shim B., Lee G., Han J., Jeon J.-K. Synthesis of High-energy-density Fuel through Dimerization of Bicyclo[2.2.1]hepta-2,5-diene over Co/HY Catalyst. Appl. Chem. Eng. 2018;29(2):185–190. https://doi.org/10.14478/ace.2017.1116Norton R.V., Fisher D.H. High density fuel compositions: Pat. US-4286109-A. Publ. 25.08.1981.Norton R.V., Fisher D.H. High density fuel compositions: Pat. US-4286109-A. Publ. 25.08.1981.Kim J., Shim B., Lee G., Han J., Kim J.M., Jeon J.-K. Synthesis of high-energy-density fuel over mesoporous aluminosilicate catalysts. Catal. Today. 2018;303:71–76. https://doi.org/10.1016/j.cattod.2017.08.024Kim J., Shim B., Lee G., Han J., Kim J.M., Jeon J.-K. Synthesis of high-energy-density fuel over mesoporous aluminosilicate catalysts. Catal. Today. 2018;303:71–76. https://doi.org/10.1016/j.cattod.2017.08.024Burdette G.W. Liquid hydrocarbon air breather fuel: Pat. US-441074-A. Publ. 18.10.1983.Burdette G.W. Liquid hydrocarbon air breather fuel: Pat. US-441074-A. Publ. 18.10.1983.Zou J.-J., Zhang X., Pan L. High-Energy-Density Fuels for Advanced Propulsion: Design and Synthesis. 1st ed. Wiley-VCH; 2020. 512 p.Zou J.-J., Zhang X., Pan L. High-Energy-Density Fuels for Advanced Propulsion: Design and Synthesis. 1st ed. Wiley-VCH; 2020. 512 p.Zhang C., Zhang X., Zou J., Li G. Catalytic dimerization of norbornadiene and norbornene into hydrocarbons with multiple bridge rings for potential highdensity fuels. Coord. Chem. Rev. 2021;436:213779. https://doi.org/10.1016/j.ccr.2021.213779Zhang C., Zhang X., Zou J., Li G. Catalytic dimerization of norbornadiene and norbornene into hydrocarbons with multiple bridge rings for potential highdensity fuels. Coord. Chem. Rev. 2021;436:213779. https://doi.org/10.1016/j.ccr.2021.213779Zarezin D.P., Rudakova M.A., Shorunov S.V., Sultanova M.U., Samoilov V.O., Maximov A.L., et al. Design and preparation of liquid polycyclic norbornanes as potential high performance fuels for aerospace propulsion. Fuel Processing Technology. 2022;225(3):107056. https://doi.org/10.1016/j.fuproc.2021.107056Zarezin D.P., Rudakova M.A., Shorunov S.V., Sultanova M.U., Samoilov V.O., Maximov A.L., et al. Design and preparation of liquid polycyclic norbornanes as potential high performance fuels for aerospace propulsion. Fuel Processing Technology. 2022;225(3):107056. https://doi.org/10.1016/j.fuproc.2021.107056Shi C., Xu J., Pan L., Zhang X., Zou J.-J. Perspective on synthesis of high-energy-density fuels: From petroleum to coal-based pathway. Chin. J. Chem. Eng. 2021;35(3):83–91. https://doi.org/10.1016/j.cjche.2021.05.004Shi C., Xu J., Pan L., Zhang X., Zou J.-J. Perspective on synthesis of high-energy-density fuels: From petroleum to coal-based pathway. Chin. J. Chem. Eng. 2021;35(3):83–91. https://doi.org/10.1016/j.cjche.2021.05.004Zhang X., Pan L., Wang L., Zou J.-J. Review on synthesis and properties of high-energy-density liquid fuels: Hydrocarbons, nanofluids and energetic ionic liquids. Chem. Eng. Sci. 2018;180:95–125. https://doi.org/10.1016/j.ces.2017.11.044Zhang X., Pan L., Wang L., Zou J.-J. Review on synthesis and properties of high-energy-density liquid fuels: Hydrocarbons, nanofluids and energetic ionic liquids. Chem. Eng. Sci. 2018;180:95–125. https://doi.org/10.1016/j.ces.2017.11.044Смагин В.М., Иоффе А.Э., Григорьев А.А., Стрельчик Б.С., Ермолаева Е.М., Сиротина И.Г. Получение норборнадиена важного полупродукта органического синтеза. Химическая промышленность. 1983;4:198–201.Smagin V.M., Ioffe A.E., Grigor’ev A.A., Strel’chik B.S., Ermolaeva E.M., Sirotina I.G. Preparation of norbornadiene, an important intermediate in organic synthesis. Khimicheskaya promyshlennost’ = Industry & Chemistry. 1983;4:198–201 (in Russ.).Стрельчик Б.С., Смагин В.М., Черных С.П., Темкин О.Н., Стычинский Г.Ф., Беленький В.М. Способ получения норборнадиена: пат. 2228324C1 РФ. Заявка № 2002125524/04А; заявл. 25.09.2002; опубл. 10.052004.Strel’chik B.S., Smagin V.M., Chernykh S.P., Temkin O.N., Stychinskii G.F., Belen’kii V.M. Norbornadiene preparation method: RF Pat. RU2228324C1. Publ. 10.05.2004. (in Russ.).Iaccino L.L., Lemoine R.O.V. Processes and systems for converting hydrocarbons to cyclopentadiene: Pat. WO2017078892A1. Publ. 11.05.2017.Iaccino L.L., Lemoine R.O.V. Processes and systems for converting hydrocarbons to cyclopentadiene: Pat. WO2017078892A1. Publ. 11.05.2017.Ахмедьянова Р.А., Милославский Д.Г. Получение циклопентадиена-1,3 из пиролизных фракций, содержащих дициклопентадиен. Вестник технологического университета. 2016;19(23):33–34.Akhmed’yanova R.A., Miloslavskii D.G. Obtaining cyclopentadiene-1,3 from pyrolysis fractions containing dicyclopentadiene. Vestnik tekhnologicheskogo universiteta = Bulletin of the Technological University. 2016;19(23):33–34 (in Russ.).Лиакумович А.Г., Седова С.Н., Деев А.В., Магсумов И.А., Ерхов А.В., Черезова Е.Н. Изучение особенностей стадии ректификации дициклопентадиена в смеси производственных потоков нефтехимического и коксохимического сырья при его выделении. Нефтепереработка и нефтехимия. Научно-технические достижения и передовой опыт. 2010;(12):30–33.Liakumovich A.G., Sedova S.N., Deev A.V., Magsumov I.A., Erkhov A.V., Cherezova E.N. Study of features of a stage of dicyclopentadiene rectification in a mix of industrial streams of petrochemical and cokechemical raw materials at its excretion. Neftepererabotka i neftekhimiya. Nauchno-tekhnicheskie dostizheniya i peredovoi opyt = Oil Processing and Petrochemistry. 2010;(12):30–33 (in Russ.).Muldoon J.A., Harvey B.G. Bio-Based Cycloalkanes: The Missing Link to High-Performance Sustainable Jet Fuels. ChemSusChem. 2020;13(22):5777–5807. https://doi.org/10.1002/cssc.202001641Muldoon J.A., Harvey B.G. Bio-Based Cycloalkanes: The Missing Link to High-Performance Sustainable Jet Fuels. ChemSusChem. 2020;13(22):5777–5807. https://doi.org/10.1002/cssc.202001641Harvey B.G. Cyclopentadiene fuels: Pat. US-11078139-B1. 2021.Harvey B.G. Cyclopentadiene fuels: Pat. US-11078139-B1. 2021.Дураков С.А., Шамсиев Р.С., Флид В.Р., Гехман А.Е. О механизме гидридного переноса в реакции каталитического аллилирования норборнадиена аллилформиатом. Известия Академии наук. Серия химическая. 2018;67(12):2234–2240.Durakov S.A., Shamsiev R.S., Flid V.R., Gekhman A.E. Hydride transfer mechanism in the catalytic allylation of norbornadiene with allyl formate. Russ. Chem. Bull. 2018;67(12):2234–2240. https://doi.org/10.1007/s11172-018-2361-7Дураков С.А., Шамсиев Р.С., Флид В.Р., Гехман А.Е. О механизме гидридного переноса в реакции каталитического аллилирования норборнадиена аллилформиатом. Кинетика и катализ. 2019;60(3):275–279.Durakov S.A., Shamsiev R.S., Flid V.R., Gekhman A.E. Isotope Effect in Catalytic Hydroallylation of Norbornadiene by Allyl Formate. Kinet. Catal. 2019;60(3):245–249. https://doi.org/10.1134/S0023158419030042Дураков С.А., Мельников П.В., Марцинкевич Е.М., Смирнова А.А., Шамсиев Р.С., Флид В.Р. Эффект растворителя в палладий-катализируемом аллилировании норборнадиена. Известия Академии наук. Серия химическая. 2021;70(1):113–121.Durakov S.A., Melnikov P.V., Martsinkevich E.M., Smirnova A.A., Shamsiev R.S., Flid V.R. Solvent effect in palladium-catalyzed allylation of norbornadiene. Russ. Chem. Bull. 2021;70(1):113–121. https://doi.org/10.1007/s11172-021-3064-zЭфрос И.Е., Дмитриев Д.В., Флид В.Р. Каталитические синтезы полициклических соединений на основе норборнадиена в присутствии никелевых катализаторов. VII. проблемы регио- и стереоселективности в процессах циклоприсоединения активированных олефинов к норборнадиену. Кинетика и катализ. 2010;51(3):391–395.Efros I.E., Dmitriev D.V., Flid V.R. Catalytic Syntheses of Polycyclic Compounds Based on Norbornadiene in the Presence of Nickel Catalysts. Kinet. Catal. 2010;51(3):370–374. https://doi.org/10.1134/S0023158410030079García-López J.A., Frutos-Pedreño R., Bautista D., Saura-Llamas I., Vicente J. Norbornadiene as a Building Block for the Synthesis of Linked Benzazocinones and Benzazocinium Salts through Tetranuclear Carbopalladated Intermediates. Organometallics. 2017;36(2):372–383. https://doi.org/10.1021/acs.organomet.6b00795García-López J.A., Frutos-Pedreño R., Bautista D., Saura-Llamas I., Vicente J. Norbornadiene as a Building Block for the Synthesis of Linked Benzazocinones and Benzazocinium Salts through Tetranuclear Carbopalladated Intermediates. Organometallics. 2017;36(2):372–383. https://doi.org/10.1021/acs.organomet.6b00795Егиазарян K.T., Шамсиев Р.С., Флид В.Р. Квантово-химическое исследование реакции окислительного присоединения аллилкарбоксилатов к комплексам Ni(0) и Pd(0). Тонкие Химические Технологии. 2019;14(6):56–65.Egiazaryan K.Т., Shamsiev R.S., Flid V.R. Quantum chemical investigation of the oxidative addition reaction of allyl carboxylates to Ni(0) and Pd(0) complexes. Fine Chem. Technol. 2019;14(6):56–65. https://doi.org/10.32362/2410-6593-2019-14-6-56-65Шамсиев Р.С., Флид В.Р. Квантово-химическое исследование механизма каталитического [2+2+2]-циклоприсоединения сложных эфиров акриловой кислоты к норборнадиену в присутствии комплексов никеля(0). Известия Академии наук. Серия химическая. 2013;62(11):2301–2305.Shamsiev R.S., Flid V.R. Quantum chemical study of the mechanism of catalytic [2+2+2] cycloaddition of acrylic acid esters to norbornadiene in the presence of nickel(0) complexes. Russ. Chem. Bull. 2013;62(11):2301–2305. https://doi.org/10.1007/s11172-013-0333-5Шамсиев Р.С., Дробышев А.В., Флид В.Р. Квантово-химическое исследование механизма каталитической димеризации норборнадиена в присутствии гидридного комплекса Ni(I). Журнал органической химии. 2013;49(3):358–362.Shamsiev R.S., Drobyshev A.V., Flid V.R. Quantum-chemical study on the mechanism of catalytic dimerization of norbornadiene in the presence of hydride nickel(I) complex. Russ. J. Organ. Chem. 2013;49(3):345–349. https://doi.org/10.1134/S1070428013030056Siadati S.A., Nami N., Zardoost M.R. A DFT Study of Solvent Effects on the Cycloaddition of Norbornadiene and 3,4–Dihydroisoquinoline-N-Oxide. Progress in Reaction Kinetics and Mechanism. 2011;36(3):252–258. https://doi.org/10.3184/146867811X13095326582455Siadati S.A., Nami N., Zardoost M.R. A DFT Study of Solvent Effects on the Cycloaddition of Norbornadiene and 3,4–Dihydroisoquinoline-N-Oxide. Progress in Reaction Kinetics and Mechanism. 2011;36(3):252–258. https://doi.org/10.3184/146867811X13095326582455Kuisma M.J., Lundin A.M., Moth-Poulsen K., Hyldgaard P., Erhart P. Comparative Ab-Initio Study of Substituted Norbornadiene-Quadricyclane Compounds for Solar Thermal Storage. J. Phys. Chem. C. 2016;120(7):3635–3645. https://doi.org/10.1021/acs.jpcc.5b11489Kuisma M.J., Lundin A.M., Moth-Poulsen K., Hyldgaard P., Erhart P. Comparative Ab-Initio Study of Substituted Norbornadiene-Quadricyclane Compounds for Solar Thermal Storage. J. Phys. Chem. C. 2016;120(7):3635–3645. https://doi.org/10.1021/acs.jpcc.5b11489Atta-Kumi J., Pipim G.B., Tia R., Adei E. Investigating the site-, regio-, and stereo-selectivities of the reactions between organic azide and 7-heteronorbornadiene: a DFT mechanistic study. J. Mol. Model. 2021;27(9):248. https://doi.org/10.1007/s00894-021-04857-3Atta-Kumi J., Pipim G.B., Tia R., Adei E. Investigating the site-, regio-, and stereo-selectivities of the reactions between organic azide and 7-heteronorbornadiene: a DFT mechanistic study. J. Mol. Model. 2021;27(9):248. https://doi.org/10.1007/s00894-021-04857-3Friend C.M., Xu B. Heterogeneous Catalysis: A Central Science for a Sustainable Future. Acc. Chem. Res. 2017;50(3):517–521. https://doi.org/10.1021/acs.accounts.6b00510Friend C.M., Xu B. Heterogeneous Catalysis: A Central Science for a Sustainable Future. Acc. Chem. Res. 2017;50(3):517–521. https://doi.org/10.1021/acs.accounts.6b00510Hübner S., de Vries J.G., Farina V. Why Does Industry Not Use Immobilized Transition Metal Complexes as Catalysts? Adv. Synth. Catal. 2016;358(1):3–25. https://doi.org/10.1002/adsc.201500846Hübner S., de Vries J.G., Farina V. Why Does Industry Not Use Immobilized Transition Metal Complexes as Catalysts? Adv. Synth. Catal. 2016;358(1):3–25. https://doi.org/10.1002/adsc.201500846Hu X., Yip A.C.K. Heterogeneous Catalysis: Enabling a Sustainable Future. Front. Catal. 2021;1:667675. https://doi.org/10.3389/fctls.2021.667675Hu X., Yip A.C.K. Heterogeneous Catalysis: Enabling a Sustainable Future. Front. Catal. 2021;1:667675. https://doi.org/10.3389/fctls.2021.667675Vogt C., Weckhuysen B.M. The concept of active site in heterogeneous catalysis. Nat. Rev. Chem. 2022;6(2):89–111. https://doi.org/10.1038/s41570-021-00340-yVogt C., Weckhuysen B.M. The concept of active site in heterogeneous catalysis. Nat. Rev. Chem. 2022;6(2):89–111. https://doi.org/10.1038/s41570-021-00340-yДжемилев У.М., Поподько Н.Р., Козлова Е.В. Металлокомплексный катализ в органическом синтезе. Алициклические соединения. М.: Химия; 1999. 647 с.Dzhemilev U.M., Popod’ko N.R., Kozlova E.V. Metallokompleksnyi kataliz v organicheskom sinteze. Alitsiklicheskie soedineniya ( Metal complex catalysis in organic synthesis. Alicyclic compounds). Moscow: Khimiya; 1999. 647 p. (in Russ.).Фельдблюм В.Ш. Синтез и применение непредельных циклических углеводородов. М.: Химия; 1982. 208 c.Fel’dblyum V.Sh. Sintez i primenenie nepredel’nykh tsiklicheskikh uglevodorodov ( Synthesis and application of unsaturated cyclic hydrocarbons). Moscow: Khimiya; 1982. 208 p. (in Russ.).Schrauzer G.N. On Transition Metal-Catalyzed Reactions of Norbornadiene and the Concept of π Complex Multicenter Processes. In: Eley D.D., Pines H., Weisz P.B. (Eds.). Advances in Catalysis. 1968. V. 18. P. 373–396. https://doi.org/10.1016/S0360-0564(08)60431-9Schrauzer G.N. On Transition Metal-Catalyzed Reactions of Norbornadiene and the Concept of π Complex Multicenter Processes. In: Eley D.D., Pines H., Weisz P.B. (Eds.). Advances in Catalysis. 1968. V. 18. P. 373–396. https://doi.org/10.1016/S0360-0564(08)60431-9Khan R., Chen J., Fan B. Versatile Catalytic Reactions of Norbornadiene Derivatives with Alkynes. Adv. Synth. Catal. 2020;362(8):1564–1601. https://doi.org/10.1002/adsc.201901494Khan R., Chen J., Fan B. Versatile Catalytic Reactions of Norbornadiene Derivatives with Alkynes. Adv. Synth. Catal. 2020;362(8):1564–1601. https://doi.org/10.1002/adsc.201901494Джемилев У.М., Хуснутдинов Р.И., Толстиков Г.А. Норборнадиены в синтезе полициклических напряженных углеводородов с участием металлокомплексных катализаторов. Успехи химии. 1987;56(1):65–94.Dzhemilev U.M., Khusnutdinov R.I., Tolstikov G.A. Norbornadienes in the Synthesis of Polycyclic Strained Hydrocarbons with Participation of Metal Complex Catalysts. Russ. Chem. Rev. 1987;56(1):65–94. https://doi.org/10.1070/RC1987v056n01ABEH003255Аникин О.В., Корнилов Д.А., Никитина Т.В., Киселев В.Д. Переменная активность реагентов со связями С=С и N=N в реакциях циклоприсоединения. Химическая физика. 2018;37(8):3–6.Anikin O.V., Kornilov D.A., Nikitina T.V., Kiselev V.D. Variable Activity of Reagents with C=C and N=N Bonds in Cycloaddition Reactions. Russ. J. Phys. Chem. B. 2018;12(4):595–598. https://doi.org/10.1134/S1990793118040176Chen Y., Kiattansakul R., Ma B., Snyder J.K. Transition Metal-Catalyzed [4+2+2] Cycloadditions of Bicyclo[2.2.1]hepta-2,5-dienes (Norbornadienes) and Bicyclo[2.2.2]octa-2,5-dienes. J. Org. Chem. 2001;66(21):6932–6942. https://doi.org/10.1021/jo010268oChen Y., Kiattansakul R., Ma B., Snyder J.K. Transition Metal-Catalyzed [4+2+2] Cycloadditions of Bicyclo[2.2.1]hepta-2,5-dienes (Norbornadienes) and Bicyclo[2.2.2]octa-2,5-dienes. J. Org. Chem. 2001;66(21):6932–6942. https://doi.org/10.1021/jo010268oBermeshev M.V., Chapala P.P. Addition polymerization of functionalized norbornenes as a powerful tool for assembling molecular moieties of new polymers with versatile properties. Prog. Polym. Sci. 2018;84:1–46. https://doi.org/10.1016/j.progpolymsci.2018.06.003Bermeshev M.V., Chapala P.P. Addition polymerization of functionalized norbornenes as a powerful tool for assembling molecular moieties of new polymers with versatile properties. Prog. Polym. Sci. 2018;84:1–46. https://doi.org/10.1016/j.progpolymsci.2018.06.003Petrov V.A., Vasil’ev N.V. Synthetic Chemistry of Quadricyclane. Curr. Org. Synthesis. 2006;3(2):215–259. http://doi.org/10.2174/157017906776819204Petrov V.A., Vasil’ev N.V. Synthetic Chemistry of Quadricyclane. Curr. Org. Synthesis. 2006;3(2):215–259. http://doi.org/10.2174/157017906776819204Orrego-Hernández J., Dreos A., Moth-Poulsen K. Engineering of Norbornadiene/Quadricyclane Photoswitches for Molecular Solar Thermal Energy Storage Applications. Acc. Chem. Res. 2020;53(8):1478–1487. https://doi.org/10.1021/acs.accounts.0c00235Orrego-Hernández J., Dreos A., Moth-Poulsen K. Engineering of Norbornadiene/Quadricyclane Photoswitches for Molecular Solar Thermal Energy Storage Applications. Acc. Chem. Res. 2020;53(8):1478–1487. https://doi.org/10.1021/acs.accounts.0c00235Akioka T., Inoue Y., Yanagawa A., Hiyamizu M., Takagi Y., Sugimori A. A comparative study on photocatalytic hydrogen transfer and catalytic hydrogenation of norbornadiene and quadricyclane catalyzed by [Rh6(CO)16]. J. Mol. Catal. A: Chem. 2003;202(1):31–39. https://doi.org/10.1016/S1381-1169(03)00201-2Akioka T., Inoue Y., Yanagawa A., Hiyamizu M., Takagi Y., Sugimori A. A comparative study on photocatalytic hydrogen transfer and catalytic hydrogenation of norbornadiene and quadricyclane catalyzed by [Rh6(CO)16]. J. Mol. Catal. A: Chem. 2003;202(1):31–39. https://doi.org/10.1016/S1381-1169(03)00201-2Cuppoletti A., Dinnocenzo J.P., Goodman J.L., Gould I.R. Bond-Coupled Electron Transfer Reactions: Photoisomerization of Norbornadiene to Quadricyclane. J. Phys. Chem. A. 1999;103(51):11253–11256. https://doi.org/10.1021/jp992884iCuppoletti A., Dinnocenzo J.P., Goodman J.L., Gould I.R. Bond-Coupled Electron Transfer Reactions: Photoisomerization of Norbornadiene to Quadricyclane. J. Phys. Chem. A. 1999;103(51):11253–11256. https://doi.org/10.1021/jp992884iLahiry S., Haldar C. Use of semiconductor materials as sensitizers in a photochemical energy storage reaction, norbornadiene to quadricyclane. Solar Energy. 1986;37(1):71–73. https://doi.org/10.1016/0038-092X(86)90109-XLahiry S., Haldar C. Use of semiconductor materials as sensitizers in a photochemical energy storage reaction, norbornadiene to quadricyclane. Solar Energy. 1986;37(1):71–73. https://doi.org/10.1016/0038-092X(86)90109-XGhandi M., Rahimi A., Mashayekhi G. Triplet photosensitization of myrcene and some dienes within zeolite Y through heavy atom effect. J. Photochem. Photobiol. A. 2006;181(1):56–59. https://doi.org/10.1016/j.jphotochem.2005.10.033Ghandi M., Rahimi A., Mashayekhi G. Triplet photosensitization of myrcene and some dienes within zeolite Y through heavy atom effect. J. Photochem. Photobiol. A. 2006;181(1):56–59. https://doi.org/10.1016/j.jphotochem.2005.10.033Gu L., Liu F. Photocatalytic isomerization of norbornadiene over Y zeolites. React. Kinet. Catal. Lett. 2008;95(1):143–151. https://doi.org/10.1007/s11144-008-5326-2Gu L., Liu F. Photocatalytic isomerization of norbornadiene over Y zeolites. React. Kinet. Catal. Lett. 2008;95(1):143–151. https://doi.org/10.1007/s11144-008-5326-2Zou J.-J., Zhang M.-Y., Zhu B., Wang L., Zhang X., Mi Z. Isomerization of Norbornadiene to Quadricyclane Using Ti-Containing MCM-41 as Photocatalysts. Catal. Lett. 2008;124(1–2):139–145. https://doi.org/10.1007/s10562-008-9441-5Zou J.-J., Zhang M.-Y., Zhu B., Wang L., Zhang X., Mi Z. Isomerization of Norbornadiene to Quadricyclane Using Ti-Containing MCM-41 as Photocatalysts. Catal. Lett. 2008;124(1–2):139–145. https://doi.org/10.1007/s10562-008-9441-5Zou J.-J., Liu Y., Pan L., Wang L., Zhang X. Photocatalytic isomerization of norbornadiene to quadricyclane over metal (V, Fe and Cr)-incorporated Ti–MCM-41. Appl. Catal. B. 2010;95(3):439–445. https://doi.org/10.1016/j.apcatb.2010.01.024Zou J.-J., Liu Y., Pan L., Wang L., Zhang X. Photocatalytic isomerization of norbornadiene to quadricyclane over metal (V, Fe and Cr)-incorporated Ti–MCM-41. Appl. Catal. B. 2010;95(3):439–445. https://doi.org/10.1016/j.apcatb.2010.01.024Pan L., Zou J.-J., Zhang X., Wang L. Photoisomerization of Norbornadiene to Quadricyclane Using Transition Metal Doped TiO2. Ind. Eng. Chem. Res. 2010;49(18):8526–8531. https://doi.org/10.1021/ie100841wPan L., Zou J.-J., Zhang X., Wang L. Photoisomerization of Norbornadiene to Quadricyclane Using Transition Metal Doped TiO2. Ind. Eng. Chem. Res. 2010;49(18):8526–8531. https://doi.org/10.1021/ie100841wZou J.-J., Pan L., Wang li., Zhang X. Photoisomerization of Norbornadiene to Quadricyclane Using Ti-Containing Photocatalysts. In: Saha S. (Ed.). Molecular Photochemistry – Various Aspects. 2012. P. 41–62. https://doi.org/10.5772/26597Zou J.-J., Pan L., Wang li., Zhang X. Photoisomerization of Norbornadiene to Quadricyclane Using Ti-Containing Photocatalysts. In: Saha S. (Ed.). Molecular Photochemistry – Various Aspects. 2012. P. 41–62. https://doi.org/10.5772/26597Hirao K., Yamashita A., Yonemitsu O. Cycloreversion of acylquadricyclane to acylnorbornadiene promoted by metal oxides. Tetrahedron Lett. 1988;29(33):4109–4112. https://doi.org/10.1016/S0040-4039(00)80429-3Hirao K., Yamashita A., Yonemitsu O. Cycloreversion of acylquadricyclane to acylnorbornadiene promoted by metal oxides. Tetrahedron Lett. 1988;29(33):4109–4112. https://doi.org/10.1016/S0040-4039(00)80429-3Koser G.F., Faircloth J.N. Silver(I)-promoted reactions of strained hydrocarbons. Oxidation vs. rearrangement. J. Org. Chem. 1976;41(3):583–585. https://doi.org/10.1021/jo00865a048Koser G.F., Faircloth J.N. Silver(I)-promoted reactions of strained hydrocarbons. Oxidation vs. rearrangement. J. Org. Chem. 1976;41(3):583–585. https://doi.org/10.1021/jo00865a048Ford J.F., Mann C.K., Vickers T.J. Monitoring the Heterogeneously Catalyzed Conversion of Quadricyclane to Norbornadiene by Raman Spectroscopy. Appl. Spectrosc. 1994;48(5):592–595. https://doi.org/10.1366/0003702944924907Ford J.F., Mann C.K., Vickers T.J. Monitoring the Heterogeneously Catalyzed Conversion of Quadricyclane to Norbornadiene by Raman Spectroscopy. Appl. Spectrosc. 1994;48(5):592–595. https://doi.org/10.1366/0003702944924907Manassen J. Catalysis of a symmetry restricted reaction by transition metal complexes. The importance of the ligand. J. Catal. 1970;18(1):38–45. https://doi.org/10.1016/0021-9517(70)90309-XManassen J. Catalysis of a symmetry restricted reaction by transition metal complexes. The importance of the ligand. J. Catal. 1970;18(1):38–45. https://doi.org/10.1016/0021-9517(70)90309-XMiki S., Ohno T., Iwasaki H., Yoshida Z. Cobalt(II) tetraphenylporphyrin-catalyzed isomerization of electronegative substituted quadricyclanes. Tetrahedron Lett. 1985;26(29):3487–3490. https://doi.org/10.1016/S0040-4039(00)98671-4Miki S., Ohno T., Iwasaki H., Yoshida Z. Cobalt(II) tetraphenylporphyrin-catalyzed isomerization of electronegative substituted quadricyclanes. Tetrahedron Lett. 1985;26(29):3487–3490. https://doi.org/10.1016/S0040-4039(00)98671-4Miki S., Maruyama T., Ohno T., Tohma T., Toyama S., Yoshida Z. Alumina-anchored Cobalt(II) Schiff Base Catalyst for the Isomerization of Trimethyldicyanoquadricyclane to the Norbornadiene. Chem. Lett. 1988;17(5):861–864. https://doi.org/10.1246/cl.1988.861Miki S., Maruyama T., Ohno T., Tohma T., Toyama S., Yoshida Z. Alumina-anchored Cobalt(II) Schiff Base Catalyst for the Isomerization of Trimethyldicyanoquadricyclane to the Norbornadiene. Chem. Lett. 1988;17(5):861–864. https://doi.org/10.1246/cl.1988.861Wang Z., Roffey A., Losantos R., Lennartson A., Jevric M., Petersen A.U., et al. Macroscopic heat release in a molecular solar thermal energy storage system. Energy Environ. Sci. 2019;12(1):187–193. https://doi.org/10.1039/C8EE01011KWang Z., Roffey A., Losantos R., Lennartson A., Jevric M., Petersen A.U., et al. Macroscopic heat release in a molecular solar thermal energy storage system. Energy Environ. Sci. 2019;12(1):187–193. https://doi.org/10.1039/C8EE01011KКузнецова Н.А., Калия О.Л., Леонтьева С.В., Манулик О.С., Негримовский В.М., Флид В.Р., Шамсие Р.С., Южакова О.А., Яштулов Н.А. Катализатор и способ валентной изомеризации квадрициклана в норборнадиен: пат. RU 2470030 C1 РФ. Заявка № 2011146910/04; заявл. 21.11. 2011; опубл. 20.11.2012.Kuznetsova N.A., Kaliya O.L., Leont’eva S.V., Manulik O.S., Negrimovskii V.M., Flid V.R., Shamsie R.S., Yuzhakova O.A., Yashtulov N.A. Catalyst and method for valence isomerisation of quadricyclane in norbornadiene: RF Pat. RU 2470030 C1. Publ. 20.11.1012. (in Russ.).Флид В.Р., Леонтьева С.В., Калия О.Л., Дураков С.А. Способ проведения процесса обратимой изомеризации норборнадиена в квадрициклан: пат. RU 2618527 C1 РФ. Заявка № 2015148230; заявл. 10.11. 2015; опубл. 04.05.2017.Flid V.R., Leont’eva S.V., Kaliya O.L., Durakov S.A. Method for carrying out the process of reversible isomerization of norbornadiene in a quadricyclean: RF Pat. RU 2618527 C1. Publ. 04.05.2017]. (in Russ.).Roduner E. Size matters: why nanomaterials are different. Chem. Soc. Rev. 2006;35(7):583–592. https://doi.org/10.1039/B502142CRoduner E. Size matters: why nanomaterials are different. Chem. Soc. Rev. 2006;35(7):583–592. https://doi.org/10.1039/B502142CPujari S.P., Scheres L., Marcelis A.T.M., Zuilhof H. Covalent surface modification of oxide surfaces. Angew. Chem. Int. Ed. Engl. 2014;53(25):6322–6356. https://doi.org/10.1002/anie.201306709Pujari S.P., Scheres L., Marcelis A.T.M., Zuilhof H. Covalent surface modification of oxide surfaces. Angew. Chem. Int. Ed. Engl. 2014;53(25):6322–6356. https://doi.org/10.1002/anie.201306709Luchs T., Lorenz P., Hirsch A. Efficient Cyclization of the Norbornadiene‐Quadricyclane Interconversion Mediated by a Magnetic [Fe3O4−CoSalphen] Nanoparticle Catalyst. ChemPhotoChem. 2020;4(1):52–58. https://doi.org/10.1002/cptc.201900194Luchs T., Lorenz P., Hirsch A. Efficient Cyclization of the Norbornadiene‐Quadricyclane Interconversion Mediated by a Magnetic [Fe3O4−CoSalphen] Nanoparticle Catalyst. ChemPhotoChem. 2020;4(1):52–58. https://doi.org/10.1002/cptc.201900194Lorenz P., Luchs T., Hirsch A. Molecular Solar Thermal Batteries through Combination of Magnetic Nanoparticle Catalysts and Tailored Norbornadiene Photoswitches. Chem. Eur. J. 2021;27(15):4993–5002. https://doi.org/10.1002/chem.202005427Lorenz P., Luchs T., Hirsch A. Molecular Solar Thermal Batteries through Combination of Magnetic Nanoparticle Catalysts and Tailored Norbornadiene Photoswitches. Chem. Eur. J. 2021;27(15):4993–5002. https://doi.org/10.1002/chem.202005427Suld G., Schneider A., Myers Jr H.K.M. Catalytic dimerization of norbornadiene to Binor-S: Pat. US-4031150-A. Publ. 21.06.1977.Suld G., Schneider A., Myers Jr H.K.M. Catalytic dimerization of norbornadiene to Binor-S: Pat. US-4031150-A. Publ. 21.06.1977.Warrener R.N., Butler D.N., Golic M. The synthesis of geometric variants of rigidly-linked uracil-{spacer}-uracil and uracil-{spacer}-effector molecules using block assembly methods. Nucleosides Nucleotides. 1999;18(11–12):2631–2660. https://doi.org/10.1080/07328319908044631Warrener R.N., Butler D.N., Golic M. The synthesis of geometric variants of rigidly-linked uracil-{spacer}-uracil and uracil-{spacer}-effector molecules using block assembly methods. Nucleosides Nucleotides. 1999;18(11–12):2631–2660. https://doi.org/10.1080/07328319908044631Алентьев Д.А., Джапаридзе Д.М., Бермешев М.В., Старанникова Л.Э., Филатова М.П., Ямпольский Ю.П., Финкельштейн Е.Ш. Аддитивная сополимеризация кремнийсодержащего трициклононена с димером норборнадиена-2,5. Высокомолекулярные соединения. Серия Б. 2019;61(6):475–480.Alentiev D.A., Dzhaparidze D.M., Bermeshev M.V., Starannikova L.E., Filatova M.P., Yampolskii Y.P., et al. Addition Copolymerization of Silicon-Containing Tricyclononene with 2,5-Norbornadiene Dimer. Polym. Sci. Ser. B. 2019;61(6):812–816. https://doi.org/10.1134/S1560090419060022Rosenkoetter K.E., Garrison M.D., Quintana R.L., Harvey B.G. Synthesis and Characterization of a High-Temperature Thermoset Network Derived from a Multicyclic Cage Compound Functionalized with Exocyclic Allylidene Groups. ACS Appl. Polym. Mater. 2019;1(10):2627–2637. https://doi.org/10.1021/acsapm.9b00542Rosenkoetter K.E., Garrison M.D., Quintana R.L., Harvey B.G. Synthesis and Characterization of a High-Temperature Thermoset Network Derived from a Multicyclic Cage Compound Functionalized with Exocyclic Allylidene Groups. ACS Appl. Polym. Mater. 2019;1(10):2627–2637. https://doi.org/10.1021/acsapm.9b00542Соломатин Д.В., Кузнецова О.П., Зверева У.Г., Рочев В.Я., Бекешев В.Г., Прут Э.В. Механизм образования тонкодисперсных резиновых порошков на основе тройных этилен-пропилен-диеновых вулканизатов. Химическая физика. 2016;35(7):60–70.Solomatin D.V., Kuznetsova O.P., Zvereva U.G., Rochev V.Ya., Bekeshev V.G., Prut E.V. Mechanism of formation of fine rubber powder from ternary ethylene–propylene–diene vulcanizates. Russ. J. Phys. Chem. B. 2016; 10(4): 662–671. https://doi.org/10.1134/S1990793116040102Kettles T., Tam W. Bicyclo[2.2.1] hepta-2,5-diene (Norbornadiene). In: e-EROS Encyclopedia of Reagents for Organic Synthesis. 2012. https://doi.org/10.1002/047084289X.rn01411Kettles T., Tam W. Bicyclo[2.2.1] hepta-2,5-diene (Norbornadiene). In: e-EROS Encyclopedia of Reagents for Organic Synthesis. 2012. https://doi.org/10.1002/047084289X.rn01411Mrowca J.J., Katz T.J. Catalysis of a Cycloaddition Reaction by Rhodium on Carbon. J. Am. Chem. Soc. 1966;88(17):4012–4015. https://doi.org/10.1021/ja00969a021Mrowca J.J., Katz T.J. Catalysis of a Cycloaddition Reaction by Rhodium on Carbon. J. Am. Chem. Soc. 1966;88(17):4012–4015. https://doi.org/10.1021/ja00969a021Chung H.S., Chen C.S.H., Kremer R.A., Boulton J.R., Burdette G.W. Recent Developments in High-Energy Density Liquid Hydrocarbon Fuels. Energy Fuels. 1999;13(3):641–649. https://doi.org/10.1021/ef980195kChung H.S., Chen C.S.H., Kremer R.A., Boulton J.R., Burdette G.W. Recent Developments in High-Energy Density Liquid Hydrocarbon Fuels. Energy Fuels. 1999;13(3):641–649. https://doi.org/10.1021/ef980195kГольдшлегер Н.Ф., Азбель Б.И., Исаков Я.И., Шпиро Е.С., Миначёв Х.М. Циклодимеризация бицикло[2.2.1]гепта-2,5-диена в присутствии родийцеолитных катализаторов. Известия Академии наук. Серия химическая. 1994;43(11):1913–1919. [Gol’dshleger N.F., Azbel’ B.I., Isakov Ya.I., Shpiro E.S., Minachev Kh.M. Cyclodimerization of bicyclo[2.2.1]hepta-2,5-diene in the presence of rhodiumcontaining zeolite catalysts. Russ. Chem. Bull. 1994;43(11):1802–1808. https://doi.org/10.1007/BF00696305 ]Gol’dshleger N.F., Azbel’ B.I., Isakov Ya.I., Shpiro E.S., Minachev Kh.M. Cyclodimerization of bicyclo[2.2.1]hepta-2,5-diene in the presence of rhodiumcontaining zeolite catalysts. Russ. Chem. Bull. 1994;43(11):1802–1808. https://doi.org/10.1007/BF00696305Azbel’ B.I., Gol’Dshleger N.F., Khidekel’ M.L., Sokol V.I., Porai-Koshits M.A. Cyclodimerization of bicyclo [2.2.1]hepta-2,5-diene by rhodium carboxylates. J. Molecul. Catal. 1987;40(1):57–63. https://doi.org/10.1016/0304-5102(87)80006-8Azbel’ B.I., Gol’Dshleger N.F., Khidekel’ M.L., Sokol V.I., Porai-Koshits M.A. Cyclodimerization of bicyclo [2.2.1]hepta-2,5-diene by rhodium carboxylates. J. Molecul. Catal. 1987;40(1):57–63. https://doi.org/10.1016/0304-5102(87)80006-8Юффа А.Я., Лисичкин Г.В. Гетерогенные металлокомплексные катализаторы. Успехи химии. 1978;47(8):1414–1443.Yuffa A.Y., Lisichkin G.V. Heterogeneous Metal Complex Catalysts. Russ. Chem. Rev. 1978;47(8): 751–766. https://doi.org/10.1070/RC1978v047n08ABEH002258Флид В.Р., Иванов А.В., Манулик О.С., Белов А.П. Гетерогенно-каталитическая димеризация бицикло[2.2.1]-гептадиена. Кинетика и катализ. 1994;35(5):774–775.Flid V.R., Ivanov A.V., Manulik O.S., Belov A.P. Heterogeneous catalytic dimerization of bicyclo[2.2.1] heptadiene. Kinetika i kataliz = Kinetics and Catalysis. 1994;35(5):774–775 (in Russ.).Леонтьева C.В., Дмитриев Д.В., Кацман Е.А., Флид В.Р. Каталитические синтезы полициклических соединений на основе норборнадиена в присутствии комплексов никеля. V. Содимеризация норборнадиена и метилвинилкетона на гетерогенизированных никелевых катализаторах. Кинетика и катализ. 2006;47(4):597–601.Leont’eva S.V., Dmitriev D.V., Katsman E.A., Flid V.R. Catalytic syntheses of polycyclic compounds based on norbornadiene in the presence of nickel complexes: V. Codimerization of norbornadiene and methyl vinyl ketone on heterogenized nickel catalysts. Kinet. Catal. 2006;47(4):580–584. https://doi.org/10.1134/S0023158406040148Li C., Zhang C., Liu R., Wang L., Zhang X., Li G. Heterogeneously supported active Pd(0) complex on silica mediated by PEG as efficient dimerization catalyst for the production of high energy density fuel. Mol. Catal. 2022;520:112170. https://doi.org/10.1016/j.mcat.2022.112170Li C., Zhang C., Liu R., Wang L., Zhang X., Li G. Heterogeneously supported active Pd(0) complex on silica mediated by PEG as efficient dimerization catalyst for the production of high energy density fuel. Mol. Catal. 2022;520:112170. https://doi.org/10.1016/j.mcat.2022.112170Jeong B.H., Han J.S., Jeon J.K., Park E.S., Jeong K.H. Method for Producing Norbornadiene Dimer Using Hetorogneous Catalyst: Pat. KR101616071B1. Publ. 27.04.2016.Jeong B.H., Han J.S., Jeon J.K., Park E.S., Jeong K.H. Method for Producing Norbornadiene Dimer Using Hetorogneous Catalyst: Pat. KR101616071B1. Publ. 27.04.2016.Jeong K., Kim J., Han J., Jeong B., Jeon J.K. Dimerization of Bicyclo[2.2.1.]hepta-2,5-diene Over Various Zeolite Catalysts. Top. Catal. 2017;60(9–11):743–749. https://doi.org/10.1007/s11244-017-0780-6Jeong K., Kim J., Han J., Jeong B., Jeon J.K. Dimerization of Bicyclo[2.2.1.]hepta-2,5-diene Over Various Zeolite Catalysts. Top. Catal. 2017;60(9–11):743–749. https://doi.org/10.1007/s11244-017-0780-6Kim J., Shim B., Lee G., Han J., Jeon J.-K. Synthesis of High-energy-density Fuel through Dimerization of Bicyclo[2.2.1]hepta-2,5-diene over Co/HY Catalyst. Appl. Chem. Eng. 2018;29(2):185–190. https://doi.org/10.14478/ACE.2017.1116Kim J., Shim B., Lee G., Han J., Jeon J.-K. Synthesis of High-energy-density Fuel through Dimerization of Bicyclo[2.2.1]hepta-2,5-diene over Co/HY Catalyst. Appl. Chem. Eng. 2018;29(2):185–190. https://doi.org/10.14478/ACE.2017.1116Kim J., Shim B., Lee G., Han J., Kim J.M., Jeon J.-K. Synthesis of high-energy-density fuel over mesoporous aluminosilicate catalysts. Catalysis Today. 2018;303:71–76. https://doi.org/10.1016/j.cattod.2017.08.024Kim J., Shim B., Lee G., Han J., Kim J.M., Jeon J.-K. Synthesis of high-energy-density fuel over mesoporous aluminosilicate catalysts. Catalysis Today. 2018;303:71–76. https://doi.org/10.1016/j.cattod.2017.08.024Jeong K., Kim J., Han J., Jeon J.-K. Synthesis of High-Energy-Density Fuel Through the Dimerization of Bicyclo[2.2.1]Hepta-2,5-Diene Over a Nanoporous Catalyst. J. Nanosci. Nanotechnol. 2017;17(11):8255–8259. https://doi.org/10.1166/jnn.2017.15097Jeong K., Kim J., Han J., Jeon J.-K. Synthesis of High-Energy-Density Fuel Through the Dimerization of Bicyclo[2.2.1]Hepta-2,5-Diene Over a Nanoporous Catalyst. J. Nanosci. Nanotechnol. 2017;17(11):8255–8259. https://doi.org/10.1166/jnn.2017.15097Khan N., Abhyankar A.C., Nandi T. Cyclodimerization of norbornadiene (NBD) into high energy-density fuel pentacyclotetradecane (PCTD) over mesoporous silica supported Co–Ni nanocatalyst. J. Chem. Sci. 2021;133(1):29. https://doi.org/10.1007/s12039-021-01890-wKhan N., Abhyankar A.C., Nandi T. Cyclodimerization of norbornadiene (NBD) into high energy-density fuel pentacyclotetradecane (PCTD) over mesoporous silica supported Co–Ni nanocatalyst. J. Chem. Sci. 2021;133(1):29. https://doi.org/10.1007/s12039-021-01890-wWu M.M., Xiong Y. Process for the catalytic cyclodimerization of cyclic olefins: Pat. US5545790A. Publ. 13.08.1996.Wu M.M., Xiong Y. Process for the catalytic cyclodimerization of cyclic olefins: Pat. US5545790A. Publ. 13.08.1996.Audeh C.A., Boulton J.R., Kremer R.A., Xiong Y. Heterogeneous catalytic oligomerization of norbornene: Pat. US5461181A. Publ. 24.10.1995.Audeh C.A., Boulton J.R., Kremer R.A., Xiong Y. Heterogeneous catalytic oligomerization of norbornene: Pat. US5461181A. Publ. 24.10.1995.Джемилев У.М., Кутепов Б.И., Григорьева Н.Г., Бубённов С.В., Целютина М.И., Гизетдинова А.Ф. Способ селективного получения димеров норборнена: пат. RU2505514C1 РФ. Заявка № RU2012136669/04A; заявл. 27.08.2012; опубл. 27.01.2014.Dzhemilev U.M., Kutepov B.I., Grigor’eva N.G., Bubennov S.V., Tselyutina M.I., Gizetdinova A.F. Method of selective obtaining norbornene dimers: RF Pat. RU2505514C1. Publ. 27.01. 2014. (in Russ.).Grigor’eva N.G., Bubennov S.V., Khalilov L.M., Kutepov B.I. Dimerization of norbornene on zeolite catalysts. Chinese J. Catal. 2015;36(3):268–273. https://doi.org/10.1016/S1872-2067(14)60251-5Grigor’eva N.G., Bubennov S.V., Khalilov L.M., Kutepov B.I. Dimerization of norbornene on zeolite catalysts. Chinese J. Catal. 2015;36(3):268–273. https://doi.org/10.1016/S1872-2067(14)60251-5Bubennov S.V., Grigor’eva N.G., Serebrennikov D.V., Agliullin M.R., Kutepov B.I. Oligomerization of Unsaturated Compounds in the Presence of Amorphous Mesoporous Aluminosilicates. Pet. Chem. 2019;59(7):682–690. https://doi.org/10.1134/S096554411907003XBubennov S.V., Grigor’eva N.G., Serebrennikov D.V., Agliullin M.R., Kutepov B.I. Oligomerization of Unsaturated Compounds in the Presence of Amorphous Mesoporous Aluminosilicates. Pet. Chem. 2019;59(7):682–690. https://doi.org/10.1134/S096554411907003XChen Y., Shi C., Jia T., Cai Q., Pan L., Xie J., et al. Catalytic synthesis of high-energy–density jet-fuel-range polycyclic fuel by dimerization reaction. Fuel. 2022;308:122077. https://doi.org/10.1016/j.fuel.2021.122077Chen Y., Shi C., Jia T., Cai Q., Pan L., Xie J., et al. Catalytic synthesis of high-energy–density jet-fuel-range polycyclic fuel by dimerization reaction. Fuel. 2022;308:122077. https://doi.org/10.1016/j.fuel.2021.122077Ananikov V.P., Beletskaya I.P. Toward the Ideal Catalyst: From Atomic Centers to a “Cocktail” of Catalysts. Organometallics. 2012;31(5):1595–1604. https://doi.org/10.1021/om201120nAnanikov V.P., Beletskaya I.P. Toward the Ideal Catalyst: From Atomic Centers to a “Cocktail” of Catalysts. Organometallics. 2012;31(5):1595–1604. https://doi.org/10.1021/om201120nEremin D.B., Ananikov V.P. Understanding active species in catalytic transformations: From molecular catalysis to nanoparticles, leaching, “Cocktails” of catalysts and dynamic systems. Coord. Chem. Rev. 2017;346:2–19. https://doi.org/10.1016/j.ccr.2016.12.021Eremin D.B., Ananikov V.P. Understanding active species in catalytic transformations: From molecular catalysis to nanoparticles, leaching, “Cocktails” of catalysts and dynamic systems. Coord. Chem. Rev. 2017;346:2–19. https://doi.org/10.1016/j.ccr.2016.12.021Prima D.O., Kulikovskaya N.S., Galushko A.S., Mironenko R.M., Ananikov V.P. Transition metal ‘cocktail’-type catalysis. Curr. Opin. Green Sustain. Chem. 2021;31:100502. https://doi.org/10.1016/j.cogsc.2021.100502Prima D.O., Kulikovskaya N.S., Galushko A.S., Mironenko R.M., Ananikov V.P. Transition metal ‘cocktail’-type catalysis. Curr. Opin. Green Sustain. Chem. 2021;31:100502. https://doi.org/10.1016/j.cogsc.2021.100502Cantillo D., Kappe C.O. Immobilized Transition Metals as Catalysts for Cross-Couplings in Continuous Flow—A Critical Assessment of the Reaction Mechanism and Metal Leaching. ChemCatChem. 2014;6(12):3286–3305. https://doi.org/10.1002/cctc.201402483Cantillo D., Kappe C.O. Immobilized Transition Metals as Catalysts for Cross-Couplings in Continuous Flow—A Critical Assessment of the Reaction Mechanism and Metal Leaching. ChemCatChem. 2014;6(12):3286–3305. https://doi.org/10.1002/cctc.201402483

The authors declare that there are no conflicts of interest present.