Tetrahedron

The Pummerer rearrangement of phenyl methyl sulphonium bis (methoxycarbonyl)-methylide

T Yagihara, S Oae

Index: Yagihara,T.; Oae,S. Tetrahedron, 1972 , vol. 28, p. 2759 - 2765

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Citation Number: 12

Abstract

The reaction between phenyl methyl sulphonium bis (methoxycarbonyl) methylide and either acetic anhydride or benzoyl peroxide proceeds via “Pummerer” type rearrangement to afford phenyl α-acyloxymethyl sulphide. The kinetic data suggest that the rate-determining step involves S C bond cleavage after initial acylation or acyloxylation and subsequent proton removal by acyloxy anion unlike the corresponding reaction of the analogous ...