1,3-REARRANGEMENT OF ALLYLIC SULFONES - REARRANGEMENT-CYCLIZATION OF ALLYLIC 4-PENTENYL SULFONES

被引：16

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)60462-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Allylic alkyl sulphones CH2:CHC(Me)2SO2R (R=Me, Et, iPr, tBu, Ch2SiMe3, CH2CH2SiMe3, and CH2CH(OH)Me underwent 1,3-rearrangement on treatment with benzoyl peroxide in tBuOH. 1,3-Rearrangement did not occur in cases (R=CH2Ph, CH2COMe) where the intermediate sulphonyl radical RSO2. could undergo loss of sulphur dioxide to form a resonance-stabilised alkyl radical. Allylic 4-pentenyl sulphones undergo rearrangement with accompanying cyclisation of the intermediate radical, this process is mor efficient if the allylic sulphone bears an electron withdrawing group at the beta-position.

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页码：2537 / 2540

页数：4

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