1,2-EPOXYCYCLO-OCTANES - EFFECT OF UNSATURATION ON COURSE OF RING OPENING AND REARRANGEMENT WITH ACIDS

被引:18
作者
HEAP, N
GREEN, GE
WHITHAM, GH
机构
[1] Dyson Perrins Laboratory, Oxford
来源
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC | 1969年 / 01期
关键词
D O I
10.1039/j39690000160
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The products from the reactions of 1,2-epoxycyclo-octane (I), 3,4-epoxycyclo-octene (II), and 5,6-epoxycyclo-octa-1,3-diene (III) with a number of acids in ethereal solution have been studied. It is found that the ratio of intramolecular-isomerisation reactions to ring-opening processes involving incorporation of external nucleophile, increases with increasing degree of unsaturation in the substrate. Particular attention is paid to the reaction of (III), and it is suggested that the isomerisation to cyclo-octa-2,4-dienone may involve the first example of a 1,6-sigmatropic shift in a pentadienyl cation.
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页码:160 / &
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