The chemistry of aryllead(IV) tricarboxylates. Reaction with silyl enol ethers

Abstract

The trimethylsilyl enol ether of acetophenone (1) and p-methoxyphenyllead triacetate (2) react to give (p-methoxyphenyl)phenacyllead(IV) diacetate (4) in high yield. This plumbation reaction has been studied for a number of ketone trimethylsilyl enol ethers and aryllead triacetates, and it would appear that it is probably limited to aryl ketone trimethylsilyl enol ethers. The trifluoroacetic acid catalysed break down of these α-plumbated ketones to substituted deoxybenzoins has been examined in considerable detail. The thermal decomposition of one of the lead compounds to a deoxybenzoin derivative has also been examined.