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