REACTION OF ACYLSILANES WITH SULFUR YLIDES - SELECTIVE FORMATION OF SILYL ENOL ETHERS OR BETA-KETOSILANES

Citation
T. Nakajima et al., REACTION OF ACYLSILANES WITH SULFUR YLIDES - SELECTIVE FORMATION OF SILYL ENOL ETHERS OR BETA-KETOSILANES, Tetrahedron, 49(37), 1993, pp. 8343-8358
Citations number
35
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
ISSN journal
00404020
Volume
49
Issue
37
Year of publication
1993
Pages
8343 - 8358
Database
ISI
SICI code
0040-4020(1993)49:37<8343:ROAWSY>2.0.ZU;2-H
Abstract
The reaction of acylsilanes with sulfur ylides in THF results in the f ormation of the corresponding silyl enol ethers or beta-ketosilanes. T he relative ratio of these products varies with the ylide conditions a nd the stability of ylide used. It is noteworthy that silyl enol ether s were formed under the salt-free ylide conditions, and that beta-keto silanes were yielded in the presence of soluble inorganic salts in THF , selectively. The formation of both products would be interpreted in terms of the anionotropic and cationotropic rearrangements of silyl gr oup in the reaction intermediate.