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Sulfur heterocycles. 13. Oxidative chlorination of β-thiolactones. A novel synthesis of β-(chlorosulfinyl)alkanoyl chlorides and 1,2-oxathiolan-5-one 2-oxides

  • Organic Chemistry
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Bulletin of the Russian Academy of Sciences, Division of chemical science Aims and scope

Abstract

Chlorination of β-thiolactones with chlorine or sulfuryl chloride in acetic anhydride at a reactant ratio (RR) of 1:2:1 gives β-(chlorosulfinyl)alkanoyl chlorides in 75–89% yields. Oxidative chlorination of β-thiolactones with RR of 1:3:2 affords β-(chlorosulfinyl)alkanoyl chlorides and cyclic sulfinic anhydrides (1,2-oxathiolan-5-one 2-oxides). The optimum RR for the preparation of 1,2-oxathiolan-5-one 2-oxides is 1:2:2. Hydrolysis of α-chloro-β-(chlorosulfinyl)carbonyl chlorides has given novel α-chlorinated sulfinocarboxylic acids.

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Authors
  1. T. P. Vasil'eva
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Additional information

For communication 12, see [1].

A. N. Nesmeyanov Institute of Heteroorganic Chemistry, Russian Academy of Sciences, 117813 Moscow. Translated from Izvestiya Akademii Nauk, Seriya Khimicheskaya, No. 9, pp. 2153–2158, September, 1992.

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Vasil'eva, T.P. Sulfur heterocycles. 13. Oxidative chlorination of β-thiolactones. A novel synthesis of β-(chlorosulfinyl)alkanoyl chlorides and 1,2-oxathiolan-5-one 2-oxides. Russ Chem Bull 41, 1685–1689 (1992). https://doi.org/10.1007/BF00863593

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  • DOI: https://doi.org/10.1007/BF00863593

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