Synthesis and reactivity of benzylic sulfonium salts: benzylation of phenol and thiophenol under near-neutral conditions

J Forrester, RVH Jones, L Newton, PN Preston

Index: Forrester; Jones; Newton; Preston Tetrahedron, 2001 , vol. 57, # 14 p. 2871 - 2884

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Citation Number: 26

Abstract

A series of benzyldimethylsulfonium-and related hydrogensulfate salts have been synthesized from the ternary system ArCH2OH: H2SO4: Me2S or tetrahydrothiophene. The salts are generally stable crystalline solids, but anomalously high reactivity is observed for 9- (anthrylmethyl) dimethylsulfonium hydrogensulfate. Selected sulfonium salts have been used for the O-and S-benzylation of phenol and thiophenol, respectively, in a two phase ...