5-ENDO RING CLOSURES OF ALLYLIC HYDROPEROXIDES - USEFUL ROUTES TO 1,2-DIOXOLANES INVOLVING STRONGLY STEREOSELECTIVE FREE-RADICAL AND POLAR REACTIONS

被引：10

作者：

COURTNEIDGE, JL

BUSH, M

LOH, LS

机构：

[1] The Malaysian Rubber Producers Research Association Brickendonbury, Hertford

来源：

TETRAHEDRON | 1992年 / 48卷 / 18期

关键词：

D O I：

10.1016/S0040-4020(01)92274-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Intramolecular cyclisation of simple allylic hydroperoxides to give substituted 1,2-dioxolanes using electrophilic reagents has been investigated. Closure using mercury(II) acetate and electrophilic halogen reagents (NBS, Br2 and ButOCl) occurs by Markovnikov-directed and conformationally strict stereospecificity. Subsequent free- radical reaction of the mercurated dioxolanes involved specific reaction involving reaction from the sterically unprotected face of the intermediate dioxolanyl radical.

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收藏

页码：3835 / 3856

页数：22

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