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

Authors

Nicholas S. Macarthur, Clark University
Linshu Wang, Clark University
Blaine G. Mccarthy, Clark University
Charles E. Jakobsche, Clark UniversityFollow

Document Type

Article

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.

Publication Title

Synthetic Communications

Publication Date

9-2-2015

Volume

45

Issue

17

First Page

2014

Last Page

2021

ISSN

0039-7911

DOI

10.1080/00397911.2015.1061672

Keywords

Alcohol, dichloroacetamide, nitrosoamide, nitrosylation, rearrangement

Repository Citation

Macarthur, Nicholas S.; Wang, Linshu; Mccarthy, Blaine G.; and Jakobsche, Charles E., "Using N-nitrosodichloroacetamides to conveniently convert linear primary amines into alcohols" (2015). Chemistry. 119.
https://commons.clarku.edu/chemistry/119

Cross Post Location

Student Publications