REACTION OF OZONE WITH STEROIDAL ALLYLIC ALCOHOLS - EVIDENCE FOR INTRAMOLECULAR INTERCEPTION OF THE CRIEGEE CARBONYL-CARBONYL OXIDE INTERMEDIATE

被引：7
作者：
PARYZEK, Z
MARTYNOW, J
SWOBODA, W
机构：
[1] Faculty of Chemistry, Adam Mickiewicz University
来源：
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1990年 / 04期
关键词：
D O I：
10.1039/p19900001220
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The reaction of 3β-acetoxycholest-5-en-7β-ol with ozone at -70°C gives 3β-acetoxy-7β-hydroxy-5,7aβ-epoxy-5β-B-homo- 6-oxacholestane (3) and 3β-acetoxy-7β-hydroperoxy-5,7aβ-epoxy- 5β-B-homo-6-oxacholestane (11) resulting from the interception of a classical carbonyl/carbonyl oxide intermediate by intramolecular nucleophilic attack of the allylic hydroxy group on the carbonyl carbon atom. It is shown also that the two possible modes of cleavage of the primary ozonide are realized.
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页码：1220 / 1221
页数：2
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