THE GENERATION AND REARRANGEMENT OF 2-(DIAZOACETYL)CYCLOBUTANONES - THE FORMATION OF 5-SPIROCYCLOPROPYL-2(5H)-FURANONES

被引：23
|
作者：
MILLER, RD
THEIS, W
HEILIG, G
KIRCHMEYER, S
机构：
[1] IBM Research Division, Almaden Research Center, San Jose, California 95120-6099
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 04期
关键词：
D O I：
10.1021/jo00004a022
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We describe here a simple synthesis of 2-(diazoacetyl)cyclobutanones and their facile thermal rearrangement to 5-spirocyclopropyl-DELTA-alpha,beta-butenolides. The yield of the rearrangement product is high, and the reaction is completely stereospecific. alpha-Ketenylcyclobutanones have been identified spectroscopically as intermediates, and their rearrangement was studied kinetically. A strained dipolar cyclic transition is proposed for the rearrangement of the alpha-ketenylcyclobutanones to the corresponding 5-spirocyclopropyl-DELTA-alpha,beta-butenolides.
引用
收藏
页码：1453 / 1463
页数：11
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