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
收藏
页码：425 / 428
页数：4
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