Unexpected metal-free transformation of gem-Dibromomethylenes to ketones under acetylation conditions

Abstract

Novel conditions for the transformation of gem-dibromomethylenes to ketones are described. gem-Dibromo compounds were treated with acetic anhydride and triethylamine in dichloromethane/water at room temperature under an air atmosphere to give the corresponding ketones in moderate yields. A radical mechanism is proposed based on experimental results.

Keywords: dehalogenation; gem-dibromomethylenes; ketones; radical reactions; synthetic methods.