Abstract

UV photolysis of diazo(pentamethyldisilanyl)methyl ketones 1b – d generates acylsilenes (3-oxo-1-sila-1-propenes) 3 as reactive intermediates, which can be trapped by enolizable carbonyl compounds in an ene-type reaction. With non-enolizable carbonyl compounds or ethyl acetate, they undergo a [4 + 2] cycloaddition. In contrast to the photolysis in the absence of these carbonyl compounds, a Wolff rearrangement of 1b – d (or the derived carbenes) to silyl ketenes 5b – d is observed as a competitive reaction.

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