FREE-RADICAL REARRANGEMENT OF UNSATURATED SULFONES INVOLVING AN INTRAMOLECULAR HYDROGEN ABSTRACTION

被引：15

作者：

PHILLIPS, ED ^{[1
]}

WHITHAM, GH ^{[1
]}

机构：

[1] DYSON PERRINS LAB,S PARKS RD,OXFORD OX1 3QY,ENGLAND

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 15期

关键词：

D O I：

10.1016/S0040-4039(00)60463-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

5-(p-Tolunesulphonyl)-1-alkenes CH2=CHCH2CH2CH(SO2pTol)CHR1R2 (R1=Ph or Me, R2=OH; or R1=R2=Me) underwent rearrangement to give pTolSO2CH2CH2CH2CH2CH=CR1R2 (which tautomerise to ketones when R2=OH) upon treatment with benzoyl peroxide in tBuOH or pTolSO2Na inaqueous AcOH. The relative reactivities of the substrates can be rationalised in terms of the proposed reaction mechanism, namely a free radical chain involving, as propagating steps, sulphonyl radical addition to the double bond of the sulphone, 1,5-hydrogen shift, and beta-scission of the resulting beta-sulphonyl alkyl radical.

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页码：2541 / 2544

页数：4

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