Synthesis of symmetrical disulfides by reaction of fluorine-containing thiiranes with cyclic amines

S. A. Nalet’ko; T. I. Gorbunova; M. G. Pervova; M. I. Kodess; A. Ya. Zapevalov; V. I. Saloutin

doi:10.1134/S1070428017040030

Synthesis of symmetrical disulfides by reaction of fluorine-containing thiiranes with cyclic amines

Authors: Nalet’ko S.A.¹, Gorbunova T.I.¹, Pervova M.G.¹, Kodess M.I.¹, Zapevalov A.Y.¹, Saloutin V.I.¹
Affiliations:
1. Postovskii Institute of Organic Synthesis, Ural Branch
Issue: Vol 53, No 4 (2017)
Pages: 514-519
Section: Review
URL: https://bakhtiniada.ru/1070-4280/article/view/216041
DOI: https://doi.org/10.1134/S1070428017040030
ID: 216041

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Abstract

Regioselective opening of the thiirane ring in fluorine-containing thioglycidyl ethers and [(perfluorobutyl) methyl]thiirane by the action of cyclic amines afforded 1,2-aminothiols which were oxidized in situ to symmetrical disulfides. The rate of formation of the latter depended on the amine basicity. According to the NMR data, the resulting disulfides were mixtures of erythro and threo diastereoisomers.