Using N-nitrosodichloroacetamides to conveniently convert linear primary amines into alcohols

Article abstract of DOI:10.1080/00397911.2015.1061672

The reported rearrangement of N-nitrosodichloroacetamides provides a practicalmethod for converting primary amines into primary alcohols. The reaction sequence is operationally simple, requires only a single purification, and is compatible with a number of common functional groups. Mechanistic studies of the nitrosylation and rearrangement reactions illustrate the increased utility of dichloroacetamides compared to various other amides for this transformation.