Using N-Nitrosodichloroacetamides to Conveniently Convert Linear Primary Amines into Alcohols

Abstract

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.

GRAPHICAL ABSTRACT

Keywords:

• Alcohol
• dichloroacetamide
• nitrosoamide
• nitrosylation
• rearrangement

Supplemental Material

Tabulated comparisons of the reactivities of different substrates in the rearrangement and nitrosylation reactions, full experimental details, analytical data, and NMR spectra for this article can be accessed on the publisher’s website.