A tin hydride designed to facilitate removal of tin species from products of stannane-mediated radical reactions

被引：59

作者：

Clive, DLJ ^{[1
]}

Wang, J ^{[1
]}

机构：

[1] Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 04期

关键词：

D O I：

10.1021/jo010885c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stannane 1, which is simple to prepare, behaves like the conventional reagents BU3SnH and Ph3SnH in standard free radical reactions, but with the special characteristic that the tin-containing byproducts are easily and very largely removed by mild hydrolysis (LiOH-water-THF or TsOHwater-THF), which converts them into base-soluble (aqueous NaHCO3) materials. The performance of stannane 1 was evaluated for a range of radical reactions involving halides, selenides, Barton-McCombie deoxygenation, and enyne cyclization. In several cases the effectiveness of the workup procedure in removing tin species was monitored by H-1 NMR.

引用

页码：1192 / 1198

页数：7

共 108 条

[61] Hypophosphorous acid mediated dehalogenation in water [J].