Lithiation of Alkoxyalkyl Phenyl Sulfones. New Approach to Acyl Anion Synthesis

Abstract (1-Ethoxyethoxy)methyl and 1-(1-ethoxyethoxy)ethyl phenyl sulfones undergo metalation with LDA in THF in the presence of HMPA. The resulting lithium salts were easily alkylated with various alkyl halides and hydrolyzed under mild conditions to give the corresponding carbonyl compounds. The new synthetic method for the preparation of aldehydes and ketones employing these carbanions has been developed.