The reactions of aryloxysulphoxonium salts with amines and other nucleophiles

Abstract

Aryloxysulphoxonium salts, easily accessible from diazonium salts and sulphonyl compounds, are effective electrophiles. With aliphatic primary and secondary amines they react by attack on sulphur, to give a range of sulphur–nitrogen compounds, including derivatives of quinquevalent cationic sulphur; oxygen nucleophiles usually react similarly. Otherwise unreactive bases, e.g. tertiary amines, give ylides, which may rearrange to give hydroxysulphoxides. Attack may also occur at aliphatic carbon. Qualitative or semiquantitative conclusions are reached on the mechanisms of the reactions reported.