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Synthesis 2008(21): 3443-3446  
DOI: 10.1055/s-0028-1083190
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Facile Conversion of Dithioesters into Carboxylic Acids or Esters Using Alkaline Hydrogen Peroxide

Fabienne Grellepois*, Charles Portella
CNRS UMR 6229, UFR des Sciences Exactes et Naturelles, Bâtiment 18, BP 1039, 51687 Reims Cedex 2, France
Fax: +33(3)26913166; e-Mail: fabienne.grellepois@univ-reims.fr;
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Publication History

Received 30 May 2008
Publication Date:
16 October 2008 (online)

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Abstract

Simple, mild, and environmentally friendly procedures for the direct conversion of dithioesters into either carboxylic acids or esters using hydrogen peroxide under alkaline conditions are described.

Key words

desulfurization - oxidation - peroxides - carboxylic acids­ - esters

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18

Aqueous hydrogen peroxide could be replaced by solid urea-hydrogen peroxide adduct (UHP). Under these conditions, acid 4 was isolated in 88% yield.

19

All aliquots were acidified before analysis by GC/MS. Intermediates were identified by comparison of analytical data (t R, MS peaks) with those of authentic samples of dithioester 3, acid 4, ester 5, thiolester 6, thionoester 7, sulfine 8, and dibenzyl disulfide.

31

Despite the fact that only 1 equiv of base is required, using a larger amount reduced the reaction time (1 h instead of 15 h).

32

Aqueous hydrogen peroxide could be replaced by solid urea-hydrogen peroxide adduct (UHP). Under these conditions, ester 5 was isolated in 50% yield.