Conclusions
-
1.
Nucleophilic cleavage of the thiirane ring in 3-(R-o-carboranyl)-1,2-epithiopropanes by sodium thiophenoxide, potassium hydrosulfide, N-methylaniline, and lithio-1-phenyl-o-carborane proceeds regioselectively at the sterically less-hindered carbon atom.
-
2.
Treatment of 3-(R-o-carboranyl)-1,2-epithiopropanes with EtMgBr or Ph3P results in desulfurization to give the corresponding allyl-o-carboranes.
-
3.
Treatment of 3-(R-o-carboranyl)-1,2-epithiopropanes with sodium ethoxide affords oligomeric polysulfides.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature cited
A. V. Fokin and A. F. Kolomiets, The Chemistry of Thiiranes [in Russian], Nauka, Moscow (1978), p. 232.
R. N. Grimes, Carboranes, Academic Press (1970).
L. I. Zakharkin, T. V. Shustova, and A. V. Kazantsev, Zh. Obshch. Khim.,51, 1071 (1981).
D. D. Reynolds, D. Z. Fields, and D. Z. Johnson, J. Org. Chem.,25, 5130 (1961).
L. I. Zakharkin, S. A. Babich, L. E. Litovchenko, and N. N. Ivanova, Zh. Obshch. Khim.,43, 2389 (1973).
Author information
Authors and Affiliations
Additional information
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimichskaya, No. 9, pp. 2134–2137, September, 1982.
Rights and permissions
About this article
Cite this article
Kazantsev, A.V., Pustova, T.V. & Zakharkin, L.I. Reactions of 3-(R-o-carboranyl)-1,2-epithiopropanes with some nucleophiles. Russ Chem Bull 31, 1884–1887 (1982). https://doi.org/10.1007/BF00952394
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00952394