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[3] and the Eschenmoser–Tanabe fragmentation.[4][5] This reagent can be prepared by reaction of tosyl chloride with hydrazine.[6]

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. ^ Shapiro, Robert H. (1976). "Alkenes from Tosylhydrazones". Org. React. 23 (3): 405–507. doi:10.1002/0471264180.or023.03. 
  4. ^ Schreiber, J.; Felix, D.; Eschenmoser, A.; Winter, M.; Gautschi, F.; Schulte-Elte, K. H.; Sundt, E.; Ohloff, G.; Kalovoda, J.; Kaufmann, H.; Wieland, P.; Anner, G. (1967). "Die Synthese von Acetylen-carbonyl-Verbindungen durch Fragmentierung von α-β-Epoxy-ketonen mit p-Toluolsulfonylhydrazin. Vorläufige Mitteilung". Helv. Chim. Acta (in German). 50 (7): 2101–2108. doi:10.1002/hlca.19670500747. 
  5. ^ Tanabe, Masato; Crowe, David F.; Dehn, Robert L. (1967). "A novel fragmentation reaction of α,β-epoxyketones the synthesis of acetylenic ketones". Tetrahedron Lett. 8 (40): 3943–3946. doi:10.1016/S0040-4039(01)89757-4. 
  6. ^ Friedman, Lester; Litle, Robert L.; Reichle, Walter R. (1960). "p-Toluenesulfonylhydrazide". Organic Syntheses. 40: 93. ; Collective Volume, 5, p. 1055