A NOVEL 1,3-O-]C SILYL SHIFT AND DEACYLATION REACTION MEDIATED BY TETRA-N-BUTYLAMMONIUM FLUORIDE IN AN AROMATIC SYSTEM

被引：17

作者：

HE, HM

FANWICK, PE

WOOD, K

CUSHMAN, M

机构：

[1] PURDUE UNIV,DEPT MED CHEM & PHARMACOGNOSY,W LAFAYETTE,IN 47907

[2] PURDUE UNIV,DEPT CHEM,W LAFAYETTE,IN 47907

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 18期

关键词：

D O I：

10.1021/jo00123a029

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel 1,3 O --> C migration of a silyl group accompanied by a deacylation reaction was discovered during the conversion of 2-acetyl-3,17-bis(tert-butyldimethylsilyl)-beta-estradiol (4) and 3,17-bis(tert-butyldimethylsilyl)-2-propionyl-beta-estradiol (5) to 2,17-bis(tert-butyldimethylsilyl)-beta-estradiol (6) in the presence of tetra-n-butylammonium fluoride. A crossover experiment indicated that the transformation is intramolecular.

引用

页码：5905 / 5909

页数：5

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