Conversion of N-arylglycolohydroxamic acids to 1,2,3-oxathiazolidin-4-one 2,2-dioxides

N-Arylglycolohydroxamic acids 1A are converted by in situ prepared 2,2′-dipyridyl sulfite to 1,2,3-oxathiazolidin-4-one 2,2-dioxides 5 , the formation of which can be rationalized via a radical pair mechanism. The alkylating potential of the heterocyclic system 5 is demonstrated by the alkaline ethanolysis giving rise to the open chained 2-ethoxypropionanilide 6 .