Conclusions
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1.
During isomerization of cis, trans, trans-l,5,9-cyclododecatriene under the action of polyphosphoric acid mainly 1a,3,4,5,6,7,8,8a- and 2a,3,4,5,6,7,8-octahydroacenaphthenes are obtained, and under the action of i-Bu3Al formation of tricyclo[7.3.0.O2,6]dodecenes is observed. A new catalytic system Cp2TiCl2-i-Bu3Al is proposed for isomerization of the latter type.
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2.
Two new methods for obtaining 1,3-dimethyladamantane from cis,trans,trans-l,5,9-cyclododecatriene are proposed.
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Literature cited
R. C. Fort, Adamantane. The Chemistry of Diamond Molecules, New York (1976).
A. Schneider, R. W. Warren, and E. J. Janoski, J. Am. Chem. Soc.,86, 5365 (1964); H. J. Robinson and H. J. Tarratt, Tetrahedron Lett., 5 (1968).
G. A. Tolstikov, V. P. Yur'ev, I. M. Salimgareeva, and A. V. Kuchin, Izv. Akad. Nauk SSSR, Ser. Khim., 1631 (1974).
H. Antropinsova, K. Mach, V. Hanns, F. Turecek, and P. Sedmera, React. Kinet. Catal. Lett.,10, 297 (1979).
B. G. Gavrilov, O. S. Kosnikovskaya, and T. N. Nikolaeva, Zh. Prikl. Khim.,57, No. 2, 469 (1984).
W. E. Wellman, M. C. Brenneman, and M. S. Konecky, J. Org. Chem.,30, 1482 (1965).
F. Turecek, V. Hanus, P. Sedmera, H. Antropinsova, and K. Mach, Tetrahedron,35, 1463 (1979).
V. P. Yur'ev, A. V. Kuchin, I. M. Salimgareeva, G. A. Kozhevnikova, V. I. Kleiner, and G. A. Tolstikov, Izv. Akad. Nauk SSSR, Ser. Khim., 2553 (1974).
M. S. Konecky, US Patent No. 3703361; Chem. Abstrs., 1973, vol. 78, 99974r.
R. T. Arnold and E. Rondestvedt, J. Am. Chem. Soc.,67, 1265 (1945).
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10, pp. 2256–2259, October, 1986.
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Zakharkin, L.I., Zhigareva, G.G., Pryanishnikov, A.P. et al. Formation of 1,3-dimethyladamantane from cis, trans, trans-1,5,9-cyclododecatriene. Russ Chem Bull 35, 2061–2064 (1986). https://doi.org/10.1007/BF00957524
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DOI: https://doi.org/10.1007/BF00957524