Alkoxycarbenes from the thermolysis of silyl ketals

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Abstract
It is shown that α,α-dimethoxybenzylsilanes thermally rearrange to give methoxysilanes and phenylmethoxycarbene; the latter species has been trapped by a variety of reagents. The rearrangement involves retention of configuration at an asymmetric silicon center. While α,α-dimethoxyethylsilanes eliminate methanol when heated, methoxybenzhydrylsilanes rearrange to methoxysilane and diphenylcarbene but monomethoxybenzylsilanes or 2-silyldioxolanes do not thermally rearrange up to 250°.

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