Inhibition of stannane-mediated radical rearrangements by a recoverable, minimally fluorous selenol

被引：21

作者：

Crich, D ^{[1
]}

Hao, XL ^{[1
]}

Lucas, MA ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, Chicago, IL 60607 USA

来源：

ORGANIC LETTERS | 1999年 / 1卷 / 02期

关键词：

D O I：

10.1021/ol990590+

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The preparation of a minimally fluorous diaryl diselenide is described. It is demonstrated that this diselenide, reduced in situ to the corresponding selenol, may be used in conjunction with stannanes to prevent a number of radical rearrangements. A 1 M solution of this selenol used in admixture with Breslow's water-soluble stannane can be used to significantly inhibit a cyclopropylcarbinyl ring opening. The combination of the fluorous selenol and the polar stannane permits recovery of the selenol by continuous fluorous extraction and isolation of a stannane-free hydrocarbon product.

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收藏

页码：269 / 271

页数：3

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