Cationic Carbon to Nitrogen Rearrangements in the Reactions of N-(Sulfonyloxy)amines with Aldehydes

Article abstract of DOI:10.1021/jo00042a032

A series of aromatic and aliphatic aldehydes was reacted with N-((p-nitrobenzenesulfonyl)oxy)methylamine in chloroform.Products resulting from both carbon migration and hydride migration to nitrogen were isolated.The ratios of carbon to hydride migration products were used to clarify the reaction mechanism.The results support a two-step process in which cationic carbon to nitrogen rearrangements is rate determining.