STEROIDS .80. EFFECT OF C-12 SUBSTITUTION ON REACTIVITY OF DELTA16-20-KETO STEROIDS TOWARD 1,4-NUCLEOPHILIC ADDITION

被引:6
作者
ABERNETHY, GS
WALL, ME
机构
[1] Chemistry and Life Sciences Laboratory, Research Triangle Institute, Research Triangle Park
关键词
D O I
10.1021/jo01258a016
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The presence of a ketone function at C-12 has a marked rate accelerating effect on 1,4 additions to Δ16-20-keto steroids. The rates of the base-catalyzed 1,4 addition of methanol to a wide variety of 12-substituted Δ16-20-keto steroids have been measured. On the basis of nmr and ultraviolet spectral data it is concluded that the rapid rate of reaction exhibited by the 12-keto steroids is anomalous. A mechanism is proposed to explain the unexpected rate of 1,4 addition displayed by Δ16-12,20-diketo steroids. This effect is shown to be applicable to a number of nucleophiles, some of which undergo further reaction to produce polycyclic derivatives. © 1969, American Chemical Society. All rights reserved.
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页码:1606 / +
页数:1
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