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
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.