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

Authors
HE HM FANWICK PE WOOD K CUSHMAN M
Citation
Hm. He et al., A NOVEL 1,3-O-]C SILYL SHIFT AND DEACYLATION REACTION MEDIATED BY TETRA-N-BUTYLAMMONIUM FLUORIDE IN AN AROMATIC SYSTEM, Journal of organic chemistry, 60(18), 1995, pp. 5905-5909
Citations number
43
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
60
Issue
18
Year of publication
1995
Pages
5905 - 5909
Database
ISI
SICI code
0022-3263(1995)60:18<5905:AN1SSA>2.0.ZU;2-A
Abstract
A novel 1,3 O --> C migration of a silyl group accompanied by a deacyl ation reaction was discovered during the conversion of l-3,17-bis(tert -butyldimethylsilyl)-beta-estradiol (4) and ert-butyldimethylsilyl)-2- propionyl-beta-estradiol (5) to 2,17-bis(tert-butyldimethylsilyl)-beta -estradiol (6) in the presence of tetra-n-butylammonium fluoride. A cr ossover experiment indicated that the transformation is intramolecular .