A NOVEL SYNTHESIS OF THIOPHENES FROM ALLENIC SULFONES INVOLVING ALPHA,BETA-UNSATURATED SULFINES AS INTERMEDIATES

被引：13

作者：

BRAVERMAN, S ^{[1
]}

VANASTEN, PFTM ^{[1
]}

VANDERLINDEN, JB ^{[1
]}

ZWANENBURG, B ^{[1
]}

机构：

[1] CATHOLIC UNIV NIJMEGEN, DEPT ORGAN CHEM, NSR CTR MOLEC STRUCT DESIGN & SYNTH, 6525 ED NIJMEGEN, NETHERLANDS

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 31期

关键词：

D O I：

10.1016/S0040-4039(00)79399-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new method for the synthesis of alpha,beta-unsaturated sulfines by a Peterson alkylidenation of sulfur dioxide is described. The required alpha-silyl carbanions are generated by heteroconjugate addition of alkyllithium to alpha-trimethylsilylated allenic sulfones. The conjugated vinylsulfines thus prepared undergo a rapid and unprecedented cycloaromatization to thiophene derivatives. A mechanism for this remarkable conversion is presented.

引用

页码：3867 / 3870

页数：4

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