MECHANISM OF THE REARRANGEMENT OF 2(VINYLOXY)ALKYL TO 4-KETOBUTYL RADICALS

被引：17

作者：

CRICH, D

YAO, QW

机构：

[1] Department of Chemistry, University of Illinois at Chicago (M/C 111), Chicago, Il 60607-7061

来源：

TETRAHEDRON | 1994年 / 50卷 / 43期

关键词：

D O I：

10.1016/S0040-4020(01)89539-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The rearrangement of 2-(vinyloxy)alkyl to 4-ketobutyl radicals has been demonstrated to proceed by a two step mechanism involving initial 5-endo-trigonal cyclization to give a tetrahydrofuranyl radical which then fragments to the final radical. Fragmentation of the tetrahydrofuranyl radicals is demonstrated by their generation from the corresponding 2-(ethylthio)-tetrahydrofurans with stannanes and AIBN. The rearrangement reaction is completely blocked when the intermediate tetrahdrofuranyl radical is set up to undergo a 5-hexenyl rearrangement.

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页码：12305 / 12312

页数：8

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