The Reactions of α-Arylsulfonoxy Ketones with Nucleophiles

Article abstract of DOI:10.1021/jo00352a002

α-(p-Nitrophenyl)sulfonoxy ketones can be converted to α-hydroxy ketals and α-hydroxy ketones by reaction with potassium carbonate and basic or acidic workup, respectively.They also react with amines to give α-amino ketones in high yields.Nonnucleophilic amines give an intramolecular aromatic substitution in the derived enolate.Factors which dictate the reaction patterns in these compounds are discussed.