PHOTOCHEMICAL ACTIVATION OF TRIMETHYLSILYLMETHYL ALLYLIC SULFONES FOR INTRAMOLECULAR 4+3 CYCLOADDITION

被引：18

作者：

HARMATA, M

HERRON, BF

机构：

[1] Department of Chemistry, University of Missouri-Columbia, Columbia

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 34期

关键词：

D O I：

10.1016/S0040-4039(00)73914-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Irradiation of allylic sulfones 4-7 results in the formation of 4+3 cycloadducts 8-11. Although the yields are poor, this represents the first apparent photochemical generation of acyclic allylic cations for 4+3 cycloadditions. Mechanistically, this process is interpreted as an electron transfer process to form an internal radical cation/radical anion reactive intermediate. This eliminates p-tolylsulfinate anion to form an allylic cation which undergoes an intramolecular 4+3 cycloaddition.

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页码：5381 / 5384

页数：4

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