| Curtius rearrangement | |
|---|---|
| Named after | Theodor Curtius |
| Reaction type | Rearrangement reaction |
| Identifiers | |
| Organic Chemistry Portal | curtius-rearrangement |
| RSC ontology ID | RXNO:0000054 |
The Curtius rearrangement (or Curtius reaction or Curtius degradation), first defined by Theodor Curtius in 1885, is the thermal decomposition of an acyl azide to an isocyanate with loss of nitrogen gas.[1][2] The isocyanate then undergoes attack by a variety of nucleophiles such as water, alcohols and amines, to yield a primary amine, carbamate or urea derivative respectively.[3] Several reviews have been published.[4][5]
- ^ Curtius, Th. (1890). "Ueber Stickstoffwasserstoffsäure (Azoimid) N3H" [On hydrazoic acid (azoimide) N3H]. Berichte der Deutschen Chemischen Gesellschaft zu Berlin. 23 (2): 3023–3033. doi:10.1002/cber.189002302232.
- ^ Curtius, T. (1894). "20. Hydrazide und Azide organischer Säuren I. Abhandlung" [Hydrazides and azides of organic acids I. paper]. Journal für Praktische Chemie. 50: 275–294. doi:10.1002/prac.18940500125.
- ^ Kaiser, C.; Weinstock, J. (1988). "Amines from mixed carboxylic-carbonic anhydrides: 1-phenylcyclopentylamine". Organic Syntheses; Collected Volumes, vol. 6, p. 910.
- ^ Smith, P. A. S. (1946). "The Curtius reaction". Organic Reactions. 3: 337–449.
- ^ Scriven, Eric F. V.; Turnbull, Kenneth (1988). "Azides: their preparation and synthetic uses". Chemical Reviews. 88 (2): 297–368. doi:10.1021/cr00084a001.