Organic Chemistry Portal



Diazo Preparation via Dehydrogenation of Hydrazones with "Activated" DMSO

Muhammad I. Javed and Matthias Brewer*

*The University of Vermont, Department of Chemistry, 82 University Place, Burlington, Vermont 05405, Email:

M. I. Javed, M. Brewer, Org. Lett., 2007, 9, 1789-1792.

DOI: 10.1021/ol070515w


"Activated" dimethyl sulfoxide efficiently dehydrogenates hydrazones to the respective diazo compounds at -78C. Under optimized conditions, simple vacuum filtration provides solutions of pure diazo compounds from which stable diazo species can be isolated in high yield, or that can be directly used in subsequent reactions.

see article for more reactions

see article for more examples

Key Words

Diazo Compounds, Esters, DMSO, Oxalyl Chloride

ID: J54-Y2007-1320