Conclusions
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1.
Analysis of the1H and13C NMR spectra of the trans-isomers of β-phenylalkylthioethylenes is evidence for the steric interference with the p,π conjugation of the sulfur atom with the double bond with increased branching of the alkyl radicals, which occurs as a result of a decreased proportion of the planar s-cis conformer.
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2.
In cis-isomers of β-phenylalkylthioethylenes a conformation close to the planar strans is attained, and changes in the structural parameters of the alkyl groups do not affect the p,π conjugation of the sulfur atom with the double bond.
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V. M. Bzhezovskii, G. A. Kalabin, B. A. Trofimov, V. I. Rakhlin, R. N. Kudyakova, and R. G. Mirskov, Izv. Akad. Nauk SSSR, Ser. Khim., 1769 (1984).
B. A. Trofimov and S. V. Amosova, Divinylsulfide and Its Derivatives [in Russian], Nauka, Novosibirsk (1983), p. 173.
C. Muller, W. Schafer, A. Schweig, N. Thon, and H. J. Vermeer, J. Am. Chem. Soc.,98, 5440 (1976).
S. Samdal, H. M. Seip, and T. Torgrimsen, J. Mol. Struct.,57, 105 (1979).
V. V. Keiko, L. M. Sinegovskaya, N. A. Kalinina, N. K. Gusarova, M. L. Al'pert, and B. A. Trofimov, Zh. Obshch. Khim.,52, 875 (1982).
B. A. Trofimov, N. I. Shergina, A. S. Atavin, É. I. Kositsyna, A. V. Gusarov, and G. M. Gavrilova, Izv. Akad. Nauk SSSR, Ser. Khim., 116 (1972).
B. A. Trofimov, Yu. L. Frolov, L. M. Sinegovskaya, V. B. Modonov, É. I. Kositsyna, S. B. Amosova, N. K. Gusarova, and G. G. Efremova, Izv. Akad. Nauk SSSR, Ser. Khim., 340 (1977).
B. A. Trofimov, V. B. Modonov, Yu. L. Frolov, E. P. Vyalykh, T. N. Bazhenova, N. K. Gusarova, G. G. Efremova, S. V. Amosova, and V. V. Keiko, in: Reactions of Organic Compounds [in Russian], Vol. 1, Tartu (1976), p. 57.
B. A. Trofimov, V. B. Modonov, T. N. Bazhenova, B. I. Istomin, N. A. Nedolya, M. L. Al'pert, G. G. Efremova, and S. P. Sitnikova, Izv. Akad. Nauk SSSR, Ser. Khim., 89 (1979).
G. A. Kalabin, B. A. Trofimov, V. M. Bzhezovskii, D. F. Kushnarev, S. V. Amosova, N. K. Gusarova, and M. L. Al'pert, Izv. Akad. Nauk SSSR, Ser. Khim., 576 (1975).
G. Ceccarelli and E. Chiellini, Org. Magn. Reson.,2, 409 (1970).
G. K. Hamer, I. R. Peat, and W. F. Reynolds, Can. J. Chem.,51, 897 (1973).
G. K. Hamer, I. R. Peat, and W. F. Reynolds, Can. J. Chem.,51, 915 (1973).
V. M. Bzhezovskii, Dissertation [in Russian], Irkutsk (1977), p. 81.
T. Agawa, M. Ishikawa, M. Komatsu, and Y. Ohshiro, Bull. Chem. Soc. Jpn.,55, 205 (1982).
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For Communication 22 see [1].
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 1998–2002, September, 1984.
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Bzhezovskii, V.M., Tarasova, O.A., Trofimov, B.A. et al. Effects of conjugation by means of NMR spectroscopy Communication 23.1H and13C NMR spectra of cis- and trans-isomers of β-phenylalkylthioethylenes. Russ Chem Bull 33, 1821–1825 (1984). https://doi.org/10.1007/BF00948623
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DOI: https://doi.org/10.1007/BF00948623