Diazo preparation via dehydrogenation of hydrazones with "activated" DMSO |
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| Authors: | Javed Muhammad I Brewer Matthias |
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| Institution: | The University of Vermont, Department of Chemistry, 82 University Place, Burlington, Vermont 05405, USA. |
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| 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. |
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