Abstract
Trans-3-methylthiocaran-4-one was synthesized. Its structure was established by x-ray structural analysis. The dipole moment was determined. The molar Kerr constants were measured, and the dipole moments were determined, for α-methylthioacetone and α-methylthiocyclohexanone. It was found that the lowpolar gauche conformer at the C-S bond is realized in all cases for the acstate at the C-C(O) bond in the methylthiocarbonyl fragment.
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Literature cited
B. Kenneth and K. B. Wiberg, J. Am. Chem. Soc.,108, No. 19, 5817 (1986).
S. Butcher and E. B. Wilson, J. Chem. Phys.,40, No. 6, 1671 (1964).
E. Saegebarth and L. C. Krisher, J. Chem. Phys.,52, No. 7, 3555 (1970).
K. B. Wieberg and E. J. Martin, J. Am. Chem. Soc.,102, No. 18, 5035 (1985).
M. J. Aroney, R. J. W. Le Fevre, and A. N. Singh, J. Chem. Soc. Perkin Trans. 2, No. 1, 564 (1965).
S. A. Guerrero, J. R. T. Barros, Bl. Wladislow, et al., J. Chem. Soc. Perkin Trans. 2, No. 8, 1053 (1983).
I. Khargittai, Structural Chemistry of Compounds of Sulfur [in Russian], Nauka, Moscow (1986), p. 68.
A. N. Vereshchagin, Polarizability of Molecules [in Russian], Nauka, Moscow (1980), p. 95.
V. I. Minkin, O. A. Osipov, and Yu. A. Zhdanov, Dipole Moments in Organic Chemistry [in Russian], Leningrad (1968), p. 80.
Bl. Wladislow, H. Viertler, P. R. Olivato, et al., J. Chem. Soc. Perkin Trans. 2, No. 3, 453 (1980).
B. A. Arbuzov and Z. G. Isaeva, Usp. Khim.,45, No. 18, 1339 (1976).
A. N. Vereshchagin, Usp. Khim.,52, No. 11, 1879 (1983).
D. H. Williams and N. S. Bhacca, Tetrahedron, No. 21, 2021 (1965).
C. K. Bradsher, F. C. Brown, and R. J. Crautham, J. Am. Chem. Soc,76, No. 1, 114 (1954).
H. Brintzinger and M. Langheck, J. Chem. Ber.,86, 557 (1953).
W. C. Hamilton, Acta Crystallogr.,18, No. 13, 502 (1965).
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Deceased.
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 7, pp. 1563–1569, July, 1990.
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Kazakova, É.K., Davletshina, G.R., Vereshchagin, A.N. et al. Conformational investigation of α-methylthio-substituted acetone, cyclohexanone, and caran-4-one. Russ Chem Bull 39, 1414–1420 (1990). https://doi.org/10.1007/BF00957850
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DOI: https://doi.org/10.1007/BF00957850