Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
The Formation and Reactions of α-Keto Sulfoxide
Takanobu KumamotoTeruaki Mukaiyama
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1968 Volume 41 Issue 9 Pages 2111-2114

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Abstract

The reactions of α-keto sulfoxide, produced by the oxidation of thiolester, were studied. It was established that the oxidation of S-ethyl thiobenzoate with N-bromosuccinimide and isopropyl alcohol afforded benzoyl ethyl sulfoxide. Similarly, butyryl ethyl sulfoxide was produced by the oxidation of S-ethyl thiobutyrate with iodosobenzene. α-Keto sulfoxide, produced by the above-mentioned oxidations, reacts with alcohols, phenols, amines or sodium carboxylates to afford acylated products such as esters, amides or carboxylic anhydrides in good yields.

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