Diazo preparation via dehydrogenation of hydrazones with "activated" DMSO.
[reaction: see text] We report that "activated" dimethyl sulfoxide efficiently dehydrogenates hydrazones to the respective diazo species at -78 degrees 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.
Javed
Muhammad I
MI
The University of Vermont, Department of Chemistry, 82 University Place, Burlington, Vermont 05405, USA.
Brewer
Matthias
M
D001391:Azo Compounds / Q000737:chemistry*; D004121:Dimethyl Sulfoxide / Q000737:chemistry*; D005740:Gases; D006835:Hydrazones / Q000737:chemistry*; D006859:Hydrogen / Q000737:chemistry*; D015394:Molecular Structure
D001391:Azo Compounds; D005740:Gases; D006835:Hydrazones; D006859:Hydrogen; D004121:Dimethyl Sulfoxide