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A New Acid-catalysed Rearrangement of Thiosulphinates to α-Acetylthio-sulphoxides in Acetic Anhydride

DOI: 10.1039/P29800000432

Source and publish data:

Journal of the Chemical Society. Perkin transactions II p. 432 - 440 (1980)

Update date:2022-07-31

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Authors:

Furukawa, NaomichiFurukawa, Naomichi

Morishita, TsuyoshiMorishita, Tsuyoshi

Akasaka, TakeshiAkasaka, Takeshi

Oae, ShigeruOae, Shigeru

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Article abstract of DOI:10.1039/P29800000432

Some thiosulphinates with at least one proton on the carbon adjacent to the sulphenyl sulphur react with acetic anhydride containing acetic acid to afford the corresponding α-acetylthio-sulphoxides.The mechanism of this reaction was studied using thiosulphinates labelled with (2)H, (13)C, and (18)O.These tracer experiments demonstrated that the reaction proceeds via an initial Ei reaction to form the corresponding sulphenic acid ant thioaldehyde followed by recombination in which the sulphur atom of the sulphenic acid adds to the carbon atom of the thioaldehyde, eventually affording the rearranged α-acetylthio-sulphoxide.The formation of the sulphenic acid was confirmed by trapping it with methyl acrylate.The mechanism of the reaction is discussed.

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