New Methodology toward α,β-Unsaturated Carboxylic Acids from Saturated Acids

Li, Qingjiang; Tochtrop, Gregory P.

New Methodology toward α,β-Unsaturated Carboxylic Acids from Saturated Acids

2014

Li, Qingjiang | Tochtrop, Gregory P.

A carefully designed three-step unsaturation of carboxylic acids is described. Briefly, carboxylic acids were converted to the trifluoromethyl ketone. Subsequent treatment with selenium dioxide followed by hydrolysis afforded α,β-unsaturated carboxylic acids. The mechanism of the reported transformation was investigated, which led us to propose a novel explanation featuring selenium dioxide assisted enolizaion of a trifluoromethyl ketone followed by β-deprotonation.

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