Hydrazide

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P-toluenesulfonylhydrazide (1) and 1,3,5-triisopropylbenzenesulfonylhydrazide (2)

Hydrazides in organic chemistry are a class of organic compounds sharing a common functional group characterized by a nitrogen to nitrogen covalent bond with 4 substituents with at least one of them being an acyl group.[1] The general structure for a hydrazide is E(=O)-NR-NR2, where the R's are frequently hydrogens.[1] Hydrazides can be further classified by atom attached to the oxygen: carbohydrazides (R-C(=O)-NH-NH2), sulfonohydrazides (R-S(=O)2-NH-NH2), and phosphonic dihydrazides (R-P(=O)(-NH-NH2)2.[1] The related hydrazines do not carry an acyl group.[2] Some important members of this class are sulfonylhydrazides such as p-toluenesulfonylhydrazide which are useful reagents in organic chemistry such as in the Shapiro reaction. This reagent can be prepared by reaction of tosyl chloride with hydrazine.[3]

References[edit]

  1. ^ a b c IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version:  (2006–) "Hydrazides".
  2. ^ IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version:  (2006–) "Hydrazines".
  3. ^ Lester Friedman; Robert L. Litle; Walter R. Reichle (1960). "p-toluenesulfonylhydrazide". Org. Synth. 40: 93. ; Coll. Vol. 5, p. 1055