Thermally induced cyclobutenone rearrangements and domino reactions

被引：36

作者：

Harrowven, David C. ^{[1
]}

Pascoe, David D. ^{[1
]}

Guy, Ian L. ^{[1
]}

机构：

[1] Univ Southampton, Sch Chem, Southampton SO17 1BJ, Hants, England

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 03期

基金：

英国工程与自然科学研究理事会;

关键词：

cyclization; domino reactions; rearrangement; spiro compounds; thermochemistry;

D O I：

10.1002/anie.200603538

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Four thermal-rearrangement pathways and a domino reaction leading to quinones arise from the thermolysis of cyclobutenones. The course of vinylcyclobutenone rearrangements is dictated by the nature of the substituent, R (see scheme): a cyclopentenone arises when R is an electron-rich alkene. In other cases thermolysis gives a cyclohexadienone, which may collapse with elimination to form a quinone, or tautomerize into a hydroquinone or cyclohexenedione. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：425 / 428

页数：4

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