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
Org. Lett., 2007, 9 (9), pp 1789–1792
DOI: 10.1021/ol070515w
Publication Date (Web): April 5, 2007
Copyright © 2007 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, matthias.brewer@uvm.edu

Abstract

Abstract Image

We report that “activated” dimethyl sulfoxide efficiently dehydrogenates hydrazones to the respective diazo species at −78 °C. Under optimized conditions, triethylamine hydrochloride is removed quantitatively by vacuum filtration to provide solutions of diazo compounds. Stable diazo species can be isolated in high yield, or alternatively, the direct treatment of these solutions with carboxylic acids provides esters.

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History

  • Published In Issue April 26, 2007
  • Received February 28, 2007

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