ACID-CATALYZED CLEAVAGE OF SOME 3-SUBSTITUTED 5-ALPHA,6-ALPHA-EPOXY-7-NORANDROSTAN-17-ONES

被引：4
|
作者：
FLAIH, N
HANSON, JR
HITCHCOCK, PB
THANGAVELU, V
机构：
来源：
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1991年 / 06期
关键词：
D O I：
10.1039/p19910001497
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Crystallographic and spectroscopic studies show that treatment of 3-beta-acetoxy-5-alpha,6-alpha-epoxy-7-norandrostan-17-one with HBr in glacial acetic acid gives 3-beta-acetoxy-6-bromo and 3-beta,6-dibromo-7-norandrost-5-en-17-one and 5-beta-bromo-3-alpha,6-alpha-epoxy-7-norandrostan-17-one. Cleavage of the epoxide with periodic acid gives the 5-beta,6-alpha-diol. The corresponding 3-beta-methanesulphonate gave 3-beta,6-beta-diobromo-5-beta-methyl-7,19-dinorandrost-9-en-17-one and 1-methyl-7-norestra-1,3,5(10)-trien-17-one. The formation of these products is rationalized in terms of the various modes of collapse of a C-5 carbocation.
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页码：1497 / 1503
页数：7
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