Hydrazide

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 an hydrazide is (R1=O)R2-N-N-R3R4. A related class of compounds called hydrazines do not carry an acyl group.[2] 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

  1. ^ 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, http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv5p1055 ; Coll. Vol. 5: 1055