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

被引：25

作者：

Forrester, J

Jones, RVH

Newton, L

Preston, PN

机构：

[1] Syngenta, Grangemouth FK3 8XG, Stirling, Scotland

[2] Heriot Watt Univ, Dept Chem, Edinburgh EH14 4AS, Midlothian, Scotland

来源：

TETRAHEDRON | 2001年 / 57卷 / 14期

关键词：

sulfonium salts; benzylation; phenols; thiols;

D O I：

10.1016/S0040-4020(01)00137-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 system under near-neutral conditions. The benzylation of oximes and benzimidazole under basic conditions is also described. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：2871 / 2884

页数：14

共 53 条

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