title: Diazo preparation via dehydrogenation of hydrazones with "activated" DMSO.
abstract: [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.
authors.affiliation: The University of Vermont, Department of Chemistry, 82 University Place, Burlington, Vermont 05405, USA.
authors.forename: Muhammad I
authors.initials: MI
authors.lastname: Javed
authors.forename: Matthias
authors.initials: M
authors.lastname: Brewer
mesh_terms: D001391:Azo Compounds / Q000737:chemistry*; D004121:Dimethyl Sulfoxide / Q000737:chemistry*; D005740:Gases; D006835:Hydrazones / Q000737:chemistry*; D006859:Hydrogen / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: D001391:Azo Compounds; D005740:Gases; D006835:Hydrazones; D006859:Hydrogen; D004121:Dimethyl Sulfoxide