α-Xanthylmethyl Ketones from α-Diazo ketones

Abstract

A simple and efficient method to obtain α-xanthylmethyl ketones from α-diazo ketones is described. The reaction proceeds through a protonation/nucleophilic substitution sequence in the presence of p-toluenesulfonic acid and potassium ethyl xanthogenate as the nucleophile. As α-diazo ketones can be readily synthesized from ubiquitous carboxylic acids, a broad variety of xanthates can be obtained, including examples from naturally occurring substrates.

Key words

xanthates - α-diazo ketones - α-xanthylmethyl ketones - free radicals - nucleophilic substitution

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