New synthesis of α'-hydroxydienones

Abstract

Herein, attempted oxidation of selected allenols with PCC affording α'-hydroxydienones rather than simple oxidation products is described. The formation of the products observed is rationalized via a series of sigmatropic shifts, followed by hydrolysis.

Keywords: allenes; hydroxyketones; oxidation; rearrangement; sigmatropic rearrangement; sulfones.