Hydrazone
Hydrazones are a functional class of organic compounds formed by the condensation reaction of hydrazine (or, more usually, an N-substituted hydrazine) with an aldehyde or a ketone.[1][2]
Preparation
Substituted hydrazines will react directly with carbonyl compounds to form the corresponding hydrazone.[3] The reaction follows the normal addition–elimination mechanism for reactions at carbonyl carbon, and is acid-catalyzed.
The direct reaction cannot be used with hydrazine itself, as the hydrazone that is initially formed will react with a second equivalent of the carbonyl compound to form an azine. However the azine can be isolated, and then reacted with excess hydrazine to reform the hydrazone.[4][5]
Notes and references
Notes
References
- ↑ Glossary of class names of organic compounds and reactivity intermediates based on structure (IUPAC Recommendations 1995). Pure Appl. Chem. 1995, 67 (8-9), 1307–75 at 1341. DOI: 10.1351/pac199567081307.
- ↑ hydrazones, <http://goldbook.iupac.org/H02884.html> (accessed 20 September 2010), Compendium of Chemical Terminology Internet edition; International Union of Pure and Applied Chemistry (IUPAC).
- ↑ Stork, G.; Benaim, J. Monoalkylation of α,β-Unsaturated Ketones via Metalloenamines: 1-butyl-10-methyl-Δ1(9)-2-octalone. Org. Synth. 1977, 57, 69, <http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv6p0242>; Coll. Vol., 6, 242.
- ↑ Day, A. C.; Whiting, M. C. Acetone hydrazone. Org. Synth. 1970, 50, 3, <http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv6p0010>; Coll. Vol., 6, 10.
- ↑ Staudinger, H.; Gaule, Alice Vergleich der Stickstoff-Abspaltung bei verschiedenen aliphatischen Diazoverbindungen. Ber. Dtsch. Chem. Ges. 1916, 49 (2), 1897–1918. DOI: 10.1002/cber.19160490245.
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