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.
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页码：3867 / 3870
页数：4
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