Direct selective oxygen-assisted acylation of amines driven by metallic silver surfaces: dimethylamine with formaldehyde

Ling Zhou; Cassandra G Freyschlag; Bingjun Xu; Cynthia M Friend; Robert J Madix

doi:10.1039/b921066k

Direct selective oxygen-assisted acylation of amines driven by metallic silver surfaces: dimethylamine with formaldehyde

Chem Commun (Camb). 2010 Feb 7;46(5):704-6. doi: 10.1039/b921066k. Epub 2009 Dec 21.

Authors

Ling Zhou¹, Cassandra G Freyschlag, Bingjun Xu, Cynthia M Friend, Robert J Madix

Affiliation

¹ School of Engineering and Applied Sciences, Harvard University, 29 Oxford Street, Cambridge, MA 02138, USA.

PMID: 20087493
DOI: 10.1039/b921066k

Abstract

Facile, direct acylation of dimethylamine with formaldehyde to N,N-dimethylformamide proceeds with a selectivity approaching 100% at low oxygen concentrations on metallic silver surfaces; the reaction proceeds via nucleophilic attack of adsorbed dimethylamide on formaldehyde with subsequent beta-H elimination from the adsorbed hemiaminal.

Publication types

Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Acylation
Dimethylamines / chemistry*
Dimethylformamide
Formaldehyde / chemistry*
Formamides / chemical synthesis*
Formamides / chemistry
Molecular Structure
Oxygen / chemistry*
Silver / chemistry*
Surface Properties

Substances

Dimethylamines
Formamides
Formaldehyde
Silver
Dimethylformamide
dimethylamine
Oxygen