HOMOLYTIC SUBSTITUTION AT SELENIUM - A CONVENIENT SYNTHESIS OF BENZOSELENOPHENES

被引：37

作者：

SCHIESSER, CH

SUTEJ, K

机构：

[1] Department of Chemical Sciences, Deakin University, Geelong

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 35期

关键词：

D O I：

10.1016/S0040-4039(00)61211-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Substituted 2-benzylseleno-1-(2-iodophenyl)ethanols (6) react smoothly with tris(trimethylsilyl)silane (TTMSS) in benzene at 80-degrees (AIBN initiator) to give benzo[b]selenophenes (3) in 80-86% yield. Interestingly, when the parent selenide (6: R1 = R2 = H) is reacted with tri-n-butyltin hydride under similar conditions, 3-hydroxydihydrobenzo[b]selenophene (2: R1 =R2 = H)is isolated as the only product of radical cyclization.

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页码：5137 / 5140

页数：4

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