Norbornadiene as a Universal Substrate for Organic and Petrochemical Synthesis
DOI:
https://doi.org/10.18321/ectj549Abstract
A wide range of rare polycyclic hydrocarbons can be obtained through catalytic processes involving norbornadiene (NBD). The problem of selectivity is crucial for such reactions. The feasibility of controlling
selectivity and reaction rate has been shown for cyclic dimerization, co-dimerization, isomerization and allylation of NBD. Kinetic rules have been scrutinized. Consistent mechanisms have been proposed. Factors
affecting directions of the reactions and allowing us to obtain individual stereoisomers quantitatively, have been established. A series of novel unsaturated compounds has been synthesized; they incorporate a set of double bonds with different reactivity and can find an extremely wide range of applications.
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2. Bolshakov G.F. Chemistry and technology of components of liquid rocket fuel. (rus.) Leningrad, Khimia, 1983, 248 pp.
3. Schrauzer G.N. On Transition Metal-Catalyzed Reactions of Norbornadiene and the Concept of p-Complex Multicenter Processes. Advances in Catalysis and related Subjects.,N.-Y.,London, Academic Press, 1968, 9, p.373-396.
4. Smagin V.M., Ioffe F.E., Grigoriev A.A. Chemical Industry (Khemicheskaya Promyshlennost, rus.), 1983, No.4, p.198-201.
5. Jemilev U.M., Podpodko N.R., Kozova E.V. Metal-complex catalysis in organic synthesis. (rus.) M., Khimia, 1999,
648 pp.
6. Bren B.A., Dubonosov A.D., Minkin V.I., Chernoivanov V.A. Uspekhi Khimii (rus.), 1991, issue 60, p. 913-948.
7. Franceschi F., Floriani C. Inorganic Chemistry; 1999, 38, No.7, p.1520-1522.
8. Nishikudo T. Macromolecules, 1998, 31, No.9, p.2789-2796.
9. Flid V.R., Aranson M.V., Kozyrev A.N. Journal of general chemistry (rus.). 1992. V.62, issue 11. p.2636-2637.
10. Ballivet D., Billard C., Tkatchenko I. Inorg. Chim. Acta, 1977, 25, p.L58.
11. Langenbach H.J., Keller E., Vahrenkamp H. J. Organometal. Chem., 1979, 171, p.259.
12. Scharf H.D., Weisgerber G., Höver H. Tetrahedron Lett., 1967, N43, p.4227.
13. BRD patent 1239304 (1967); C.A., 1967, 67, 53780.
14. US Patent 3377398, 1968; U.S.C1 260-266.
15. US Patent 4094917 (1978); C.A., 1978, 89, P197060.
16. Ballivet D., Tkatchenko I. J. Mol. Catal., 1975, p.319.
17. Schrauzer G. N., Bastian B.N., Fosselius G.A. J. Amer. Chem. Soc., 1966, 88, p.4890.
18. US Patent N 3329732 (1967); Cl 260-666; C.A., 1967, 67, 90467.
19. Flid V.R., Manulik O.S., Grigorev A.A., Belov A.P. Kinetics and Catalysis, 1998, 39, #1. p. 51-55.
20. Flid V.R., Manulik O.S., Grigorev A.A., Belov A.P. Kinetics and Catalysis, 2000, 41, #5. p. 597-603.
21. Flid V.R., Kuznetsov V.B., Grigorev A.A., Belov A.P. Kinetics and Catalysis, 2000, 41, #5, p. 604-611.
22. Binger P., Schuchardt U. Angew. Chem., 1977, 89, N4, p.254-255.
23. Lucchi O.D., Licini G., Pasquato L., Senta M. Tetrahedron Lett., 1988, 29, p.831.
24. Furukawa J., Kobuke Y., Sigumoto T., Fueno T. J. Am. Chem. Soc., 1972, 94, p.3633.
25. Lautens M., Tam W., Edwards L.G. J. Chem. Soc., Perkin Trans. 1, 1994, p.2143-2144.
26. Lautens M., Tam W. Advances in Metal-Organic Chemistry, Liebeskind L.S., Ed.; JAI Press: Greenwich, 1996, p. 125-168.
27. Gugelchuk M.M., Wisner J. Organometallics, 1995, 14, p.1834-1839.
28. Flid V.R., Kuznetsov V.B., Dmitriev D.V. Kinetics and Catalysis, 1999, 40, # 3, p. 301-306.
29. Heimbach P., Meyer R.V., Wilke G. Liebigs Ann. Chem., 1975, p.743-748.
30. Misudo T., Naruse H., Kondo T., Ozaki Y., Watanabe Y. Angew. Chem., Int. Ed. Engl., 1994, 33, 580.
31. Lautens M., Tam W., Edwards L.G. J. Org. Chem., 1992, 57, p.8-9.
32. Greco A., Carbonaro A., Dall’Asta G. J. Org. Chem. 1970, 35, p.271-274.
33. Carbonaro A., Cambisi F., Dall’Asta G. J. Org. Chem., 1971, 36, p.1443-1445.
34. Doyle M.P. Chem. Rev., 1986, 86, p.919-939.
35. Lautens M., Tam W., Sood C. J. Org. Chem., 1993, 58, p.4513-4515.
36. Catellani M., Chiusoli G.P., Dradi E., Salerno G. J. Organomet. Chem., 1979, 177, p.C29-C31.
37. Jemilev U.M.,Khusnutdinov R.I., Galeev D.K., Nefedov O.M.,Tolstikov G.A. Izv. Akad. Nauk SSSR, Ser. Khim., 1987, N1, 3.138-148.
38. Fild V.R., Manulik O.S., Grogorev A.A., Belov A.P. Metalloorganicheskaya chimiya, 1991, #4, p. 864-871.
39. Flid V.R., Ivanov A.V., Manulik O.S., Belov A.P. Kinetika i Cataliz, 1994, 35, #5, p. 774-775.
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Published
20-08-2001
How to Cite
Flid, V. R., Manulik, O. S., Dmitriev, D. V., Kouznetsov, V. B., Evstigneeva, E. M., Belov, A. P., & Grigor’ev, A. A. (2001). Norbornadiene as a Universal Substrate for Organic and Petrochemical Synthesis. Eurasian Chemico-Technological Journal, 3(2), 73–90. https://doi.org/10.18321/ectj549
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