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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: matthias.breweruvm.edu

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

DOI: 10.1021/ol070515w (free Supporting Information)


Abstract

"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.

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Key Words

Diazo Compounds, Esters, DMSO, Oxalyl Chloride


ID: J54-Y2007-1320