Acyl azides are carboxylic acid derivatives with the general formula RCON3. These compounds, which are a subclass of organic azides, are generally colorless.[1]
Preparation
Typically acyl azides are generated under conditions where they rearrange to the isocyanate.[1]
Curtius, Th. (1894). "20. Hydrazide und Azide organischer Säuren I. Abhandlung". J. Prakt. Chem. (in German). 50 (1): 275–294. doi:10.1002/prac.18940500125.
Darapsky, August (1936). "Darstellung von α-Aminosäuren aus Alkyl-cyanessigsäuren". J. Prakt. Chem. (in German). 146 (8–12): 250–267. doi:10.1002/prac.19361460806.
Darapsky, August; Hillers, Dietrich (1915). "Über das Hydrazid der Cyanessigsäure, Isonitrosocyanessigsäure und Nitrocyanessigsäure". J. Prakt. Chem. (in German). 92 (1): 297–341. doi:10.1002/prac.19150920117.
References
^ a b cLwowski, Walter (1971). "Acyl azides". In Saul Patai (ed.). The Azido Group. PATAI'S Chemistry of Functional Groups. pp. 849–907. doi:10.1002/9780470771266.ch9. ISBN 9780470771679.
^Allen, C. F. H.; Bell, Alan (1944). "Undecyl isocyanate". Organic Syntheses. 24: 94. doi:10.15227/orgsyn.024.0094.
^Jang, Doo; Kim, Joong-Gon (2008). "Direct Synthesis of Acyl Azides from Carboxylic Acids by the Combination of Trichloroacetonitrile, Triphenylphosphine and Sodium Azide". Synlett. 2008 (13): 2072–2074. doi:10.1055/s-2008-1077979.
^Marinescu, Lavinia; Thinggaard, Jacob; Thomsen, Ib B.; Bols, Mikael (2003). "Radical Azidonation of Aldehydes". J. Org. Chem.68 (24): 9453–9455. doi:10.1021/jo035163v. PMID 14629171.
^Smith, Peter A. S. (1946). "The Curtius reaction". Org. React.3: 337–449. doi:10.1002/0471264180.or003.09. ISBN 0471264180.
^Scriven, Eric F. V.; Turnbull, Kenneth (1988). "Azides: Their preparation and synthetic uses". Chem. Rev.88 (2): 297–368. doi:10.1021/cr00084a001.
^Gagnon, Paul E.; Boivin, Paul A.; Craig, Hugh M. (1951). "Synthesis of Amino Acids from Substituted Cyanoacetic Esters". Can. J. Chem.29 (1): 70–75. doi:10.1139/v51-009.
^E. H. Rodd (1965). Chemistry of Carbon Compounds (2nd ed.). New York. p. 1157.{{cite book}}: CS1 maint: location missing publisher (link)
^Gagnon, Paul E.; Nadeau, Guy; Côté, Raymond (1952). "Synthesis of α-Amino Acids from Ethyl Cyanoacetate". Can. J. Chem.30 (8): 592–597. doi:10.1139/v52-071.