Literature DB >> 17408280

Diazo preparation via dehydrogenation of hydrazones with "activated" DMSO.

Muhammad I Javed1, Matthias Brewer.   

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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Year:  2007        PMID: 17408280     DOI: 10.1021/ol070515w

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  3 in total

1.  Divergent Reactivity of Rhodium(I) Carbenes Derived from Indole Annulations.

Authors:  Xiaoxun Li; Hui Li; Wangze Song; Po-Sen Tseng; Lingyan Liu; Ilia A Guzei; Weiping Tang
Journal:  Angew Chem Int Ed Engl       Date:  2015-09-07       Impact factor: 15.336

2.  Potassium N-iodo p-toluenesulfonamide (TsNIK, Iodamine-T): a new reagent for the oxidation of hydrazones to diazo compounds.

Authors:  Simon M Nicolle; Christopher J Moody
Journal:  Chemistry       Date:  2014-03-11       Impact factor: 5.236

3.  Flow chemistry as a discovery tool to access sp2-sp3 cross-coupling reactions via diazo compounds.

Authors:  Duc N Tran; Claudio Battilocchio; Shing-Bong Lou; Joel M Hawkins; Steven V Ley
Journal:  Chem Sci       Date:  2014-11-07       Impact factor: 9.825

  3 in total

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