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

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.

desulfurization - oxidation - peroxides - carboxylic acids­ - esters

References

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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.

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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.

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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).

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

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