Conclusions
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1.
A six-membered carbon ring possessing a double bond in the ring or a condensed three-membered ring takes the form of a half-chair or, in other words, a double bond and a condensed three-membered ring have an analogous influence on the configuration of a six-membered ring.
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2.
The presence of two double bonds or a double bond and a condensed three-membered ring or two condensed three-membered rings in the 1,4-position has an analogous influence on the configuration of the six-membered ring; the latter takes the form of a flattened boat. If the three-membered rings have volumious substituents, the central ring may be flat.
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Literature cited
N.V. Alekseev and A.I. Kitaigorodskii, Zh. Strukt. Khim.,4, 163 (1963).
V.A. Naumov and V. M. Bezzubov, Zh. Strukt. Khim.,8, 530 (1967).
V.A. Naumov, V.G. Dashevskii, and N. M. Zaripov, Dokl. Akad. Nauk SSSR,185, 604 (1969).
J.F. Chiang and S. H. Bauer, J. Amer. Chem. Soc.,91, 1898 (1969).
M. V. Lister, J. Amer. Chem. Soc.,63, 143 (1941).
C.W. Beckett, N.K. Freeman, and K.S. Pitzer, J. Amer. Chem. Soc.,70, 4227 (1948).
R. Bucourt and D. Hainaut, Bull. Soc. Chim. France, 1366 (1965).
B. Ottar, Acta Chem. Scand.,1, 283 (1947).
A.N. Vereshchagin, A. P. Anastas'eva, and S.G. Vul'fson, Izv. Akad. Nauk SSSR, Ser. Khim., 559 (1969).
V. A. Naumov and V. M. Bezzubov, Dokl. Akad. Nauk SSSR,193, 113 (1970).
V.A. Naumov, V.M. Bezzubov, N.M. Zaripov, and V.G. Dashevskii, Zh. Strukt. Khim.,11, 801 (1970).
W.D. Kumler, R. Boikess, P. Bruck, and S. Winstein, J. Amer. Chem. Soc.,86, 3126 (1964).
G. Dallinga and L. N. Toneman, J. Mol. Struct.,1, 117 (1967–1968).
E.W. Garbisch and M.G. Griffith, J. Amer. Chem. Soc.,90, 3590 (1968).
H. Oberhamer and S.H. Bauer, J. Amer. Chem. Soc.,91, 10 (1969).
V.G. Dashevskii, V.A. Naumov, and N.M. Zarupov, Zh. Strukt. Khim.,11, 746 (1970).
V.A. Naumov and V.M. Bezzubov, Dokl. Akad. Nauk SSSR,171, 634 (1966).
B.A. Arbuzov, V.A. Naumov, and L. F. Shartukov, Dokl. Akad. Nauk SSSR,163, 355 (1965).
B.A. Arbuzov, Yu.Yu. Samitov, and Z.G. Isaeva, Dokl. Akad. Nauk SSSR,150, 1036 (1963).
P.J. Kropp, J. Amer. Chem. Soc.,88, 4926 (1966).
B.A. Arbuzov, Yu.Yu. Samitov, A.V. Aganov, and Yu. L. Kleiman, Dokl. Akad. Nauk SSSR,184, 341 (1969).
B.A. Arbuzov, A.N. Vereshchagin, S.G. Vul'fson, and Z.G. Isaeva, Izv. Akad. Nauk SSSR, Ser. Khim., 1966 (1968).
V.A. Naumov and V.M. Bezzubov, Dokl. Akad. Nauk SSSR,186, 599 (1969).
M. Muhlstadt, H. von Phiet, and J. Graefe, Tetrahedron,24, 6075 (1968).
H. Frischleder, J. Graefe, H. von Phiet, and M. Muhlstadt, Tetrahedron,25, 2081 (1969).
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2425–2428, November, 1971.
The author would like to thank B.A. Arbuzov for Ms constant interest and attention to the work and A.N. Vereshchagin for his discussion and critical suggestions.
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Naumov, V.A. Some patterns in the geometrical structure of derivatives of cyclohexene and 1,4-cyclohexadiene. Russ Chem Bull 20, 2303–2306 (1971). https://doi.org/10.1007/BF00854301
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DOI: https://doi.org/10.1007/BF00854301