Summary
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1.
The stereochemistry of the reaction of the isomeric ω-styrylmercury bromides with bromine in various solvents was studied.
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2.
In dimethyl sulfoxide (SEl mechanism) the reaction goes with a retention of the geometric configuration, while in C6H6 and CCl4 (sR mechanism) the configuration is not retained.
Literature cited
I. P. Beletskaya, O. A. Reutov, and V. I. Karpov, Izv. AN SSSR, Otd. Khim. Nauk,1961, 1961.
I. P. Beletskaya, O. A. Reutov, and V. I. Karpov, Izv. AN SSSR, Otd. Khim. Nauk,1961, 2125.
I. P. Beletskaya, O. A. Reutov, and V. I. Karpov, Izv. AN SSSR, Otd. Khim. Nauk,1961, 2129.
I. P. Beletskaya, V. I. Karpov, and O. A. Reutov, Proceedings of the Conference on the Problems of the Application of Correlation Equations in Organic Chemistry [in Russian], Tartu (1962), p. 355.
A. N. Nesmeyanov and T. A. Kudryavtseva, Uch. Zapiski Moskov. Gosudarst. Univ.,151, 57 (1951); G. F. Wright, J. Org. Chem.,1, 457 (1936).
A. N. Nesmeyanov and A E. Borisov, Dokl. AN SSSR;60, 67 (1948).
C. Dufraisse, Compt. rend.,171, 960 (1920).
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 1707–1709, September, 1964
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Beletskaya, I.P., Karpov, V.I. & Reutov, O.A. Stereochemistry of the reaction of the cis-trans isomers of styrylmercury bromide with bromine. Russ Chem Bull 13, 1615–1617 (1964). https://doi.org/10.1007/BF00846306
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DOI: https://doi.org/10.1007/BF00846306