SYNTHESIS AND UNUSUAL BECKMANN FRAGMENTATION REACTION OF SYN-3-METHOXY-6-ALPHA,17-BETA-DIHYDROXYESTRA-1,3,5(10)-TRIEN-7-ONE OXIME

被引：12
作者：
PEJANOVIC, VM [1 ]
PETROVIC, JA [1 ]
CSANADI, JJ [1 ]
STANKOVIC, SM [1 ]
MILJKOVIC, DA [1 ]
机构：
[1] UNIV NOVI SAD, FAC SCI, DEPT CHEM, YU-21000 NOVI SAD, YUGOSLAVIA
来源：
TETRAHEDRON | 1995年 / 51卷 / 48期
关键词：
D O I：
10.1016/0040-4020(95)00871-5
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Sodium borohydride reduction of anti-3-methoxy-17 beta-hydroxyestra-1,3,5(10)-trien-6,7-dione 7-oxime (4a) afforded syn-3-methoxy-6 alpha, 17 beta-dihydroxyestra-1,3,5(10)-trien-7-one oxime (5), which in thionyl chloride at -18 degrees C underwent Beckmann fragmentation reaction to the unexpected 3-methoxy-6-oxo-17 beta-hydroxy-6,7-secoestra-1,3,5(10)-trien-7-nitrile (6). A mechanism of this fragmentation process was proposed.
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收藏
页码：13379 / 13384
页数：6
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