Abstract
The possible existence of an unusual cycle was investigated, which involved an equilibrium among α-silylalkoxides, α-siloxy carbanions, and carbonyl compounds accompanied by - SiR 3 . This postulation was supported by the product distributions of a series of control reactions: the C-deprotonation of 3-methoxybenzyl trimethylsilyl ether, the O-deprotonation of 3-methoxy-α-(trimethylsilyl)benzyl alcohol, and the 1,2-addition of 3-methoxybenzaldehyde with LiSiMe 3 . Consistent with this postulation were results from the reaction of 3-methoxybenzyl alcohol with KH and Me 3 SiSiMe 3 , giving 3-methoxybenzaldehyde (20% yield), and the reaction of α-cyclopropylbenzyl trimethylsilyl ether with LiSiMe 3 , affording cyclopropyl phenyl ketone (90% yield). © 1994 American Chemical Society.