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Synthesis 2008(21): 3443-3446
DOI: 10.1055/s-0028-1083190
DOI: 10.1055/s-0028-1083190
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkFacile Conversion of Dithioesters into Carboxylic Acids or Esters Using Alkaline Hydrogen Peroxide
Further Information
Received
30 May 2008
Publication Date:
16 October 2008 (online)
Publication History
Publication Date:
16 October 2008 (online)
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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Aqueous hydrogen peroxide could be replaced by solid urea-hydrogen peroxide adduct (UHP). Under these conditions, acid 4 was isolated in 88% yield.
19All 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.
31Despite the fact that only 1 equiv of base is required, using a larger amount reduced the reaction time (1 h instead of 15 h).
32Aqueous hydrogen peroxide could be replaced by solid urea-hydrogen peroxide adduct (UHP). Under these conditions, ester 5 was isolated in 50% yield.