Abstract
The three-dimensional structures of the products of catalytic hydrogenation of sym-octahydrothioxanthylium salts in the presence of palladium on carbon were studied by 13C NMR spectroscopy. It was shown that the reaction proceeds stereoselectively with the formation of cis-syn-cis isomers. The stereochemistry of the reduction products is in agreement with the previously proposed reaction mechanism.
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V. G. Kharchenko, O. A. Bozhenova, and A. D. Shebaldova, Zh. Org. Khim., 28, 2435 (1982).
D. K. Dalling and D. M. Grant, J. Am. Chem. Soc., 96, 1827 (1974).
F. W. Vierhapper and R. L. Willer, J. Org. Chem., 42, 4024 (1977).
P. Vanhee, F. De Pessemier, M. Anteunis, and D. Tavernier, Rec. Trav. Chim., 98, 294 (1979).
D. K. Dalling and D. M. Grant, J. Am. Chem. Soc., 94, 5318 (1972).
D. K. Dalling, D. M. Grant, and E. G. Paul, J. Am. Chem. Soc., 95, 3718 (1973).
A. A. Shcherbakov, G. G. Aleksandrov, Yu. T. Struchkov, and V. G. Kharchenko, Khim. Geterotsikl. Soedin., No. 11, 1470 (1979).
V. G. Kharchenko and A. F. Blinokhvatov, Khim. Geterotsikl. Soedin., 12, 1615 (1978).
V. V. Puchkova, E. N. Gur'yanova, V. G. Kharchenko, and A. A. Rassudova, Zh. Org. Khim., 9, 1531 (1973).
S. K. Klimenko, T. V. Stolbova, T. I. Tyrina, N. N. Sorokin, I. F. Leshcheva, N. M. Sergeev, and V. G. Kharchenko, Khim. Geterotsikl. Soedin., No. 7, 898 (1984).
S. K. Klimenko, T. V. Stolbova, T. I. Tyrina, N. N. Sorokin, and V. G. Kharchenko, Zh. Org. Khim., 21, 1918 (1985).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1187–1190, September, 1987.
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Kharchenko, V.G., Yudovich, L.M., Bozhenova, O.A. et al. Stereochemical peculiarities of the catalytic reduction of sym-octahydrothioxanthylium salts. Chem Heterocycl Compd 23, 947–950 (1987). https://doi.org/10.1007/BF00475356
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DOI: https://doi.org/10.1007/BF00475356