Organic synthesis by the pummerer reaction. III. A method for the synthesis of aldehydes.

Abstract

Aldehydes were synthesized via α-acetoxy sulfides from alkyl aryl sulfoxides by the Pummerer reaction with acetic anhydride in the presence of base. By this method, isobutyraldehyde, pentanal, benzaldehyde, and 2-acetylamino-5-methylbenzaldehyde were obtained from isobutyl phenyl sulfoxide, pentyl p-tolyl sulfoxide, benzyl phenyl sulfoxide, and 2-acetylamino-5-methylbenzyl phenyl sulfoxide, respectively. The starting sulfoxides are easily synthesized from olefins, alkyl halides, or alkyl aryl sulfides.