acyl azide

Typically acyl azides are generated under conditions where they rearrange to the isocyanate.

Alkyl or aryl acyl chlorides react with sodium azide to give acyl azides.{{OrgSynth| prep = cv3p0846 | title = Undecyl isocyanate | first1 = C. F. H. | last1 = Allen | first2 = Alan | last2 = Bell | year = 1944 | volume = 24 | pages = 94 | doi = 10.15227/orgsyn.024.0094}}{{OrgSynth | prep = cv4p0715 | title = m-Nitrobenzazide (Benzoyl azide, m-nitro-) | first = Jon | last = Munch-Petersen | year = 1953 | volume = 33 | pages = 53 | doi = 10.15227/orgsyn.033.0053}}

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The second major route to azides is from the acyl hydrazides with nitrous acid.

Acyl azides have also been synthesized from various carboxylic acids and sodium azide in presence of triphenylphosphine and trichloroacetonitrile catalysts in excellent yields at mild conditions.{{cite journal | doi = 10.1055/s-2008-1077979 | title = Direct Synthesis of Acyl Azides from Carboxylic Acids by the Combination of Trichloroacetonitrile, Triphenylphosphine and Sodium Azide | year = 2008 | last1 = Jang | first1 = Doo | last2 = Kim | first2 = Joong-Gon | journal = Synlett | volume = 2008 | issue = 13 | pages = 2072–2074}} Another route starts with aliphatic and aromatic aldehydes reacting with iodine azide which is formed from sodium azide and iodine monochloride in acetonitrile.{{cite journal | doi = 10.1021/jo035163v | title = Radical Azidonation of Aldehydes | year = 2003 | last1 = Marinescu | first1 = Lavinia | last2 = Thinggaard | first2 = Jacob | last3 = Thomsen | first3 = Ib B. | last4 = Bols | first4 = Mikael | journal = J. Org. Chem. | volume = 68 | issue = 24 | pages = 9453–9455 | pmid = 14629171 }}

On Curtius rearrangement, acyl azides yield isocyanates.{{cite journal | title = The Curtius reaction | last = Smith | first = Peter A. S. | journal = Org. React. | year = 1946 | volume = 3 | pages = 337–449 | doi = 10.1002/0471264180.or003.09| isbn = 0471264180 }}{{Cite journal | doi = 10.1021/cr00084a001 | title = Azides: Their preparation and synthetic uses | year = 1988 | last1 = Scriven | first1 = Eric F. V. | last2 = Turnbull | first2 = Kenneth | journal = Chem. Rev. | volume = 88 | issue = 2 | pages = 297–368}}

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Acyl azides are also formed in Darapsky degradation,{{cite journal | first1 = Paul E. | last1 = Gagnon | first2 = Paul A. | last2 = Boivin | first3 = Hugh M. | last3 = Craig | journal = Can. J. Chem. | volume = 29 | issue = 1 | pages = 70–75 | year = 1951 | doi = 10.1139/v51-009 | title = Synthesis of Amino Acids from Substituted Cyanoacetic Esters| doi-access = free }}{{cite book | author = E. H. Rodd | title = Chemistry of Carbon Compounds | edition = 2nd | pages = 1157 | location = New York | year = 1965}}{{cite journal | journal = Can. J. Chem. | volume = 30 | pages = 592–597 | year = 1952 | doi = 10.1139/v52-071 | title = Synthesis of α-Amino Acids from Ethyl Cyanoacetate | last1 = Gagnon | first1 = Paul E. | last2 = Nadeau | first2 = Guy | last3 = Côté | first3 = Raymond | issue = 8| doi-access = free }}

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• {{cite journal | title = Ueber Stickstoffwasserstoffsäure (Azoimid) N₃H | last = Curtius | first = Th. | authorlink = Theodor Curtius | journal = Ber. | year = 1890 | volume = 23 | issue = 2 | pages = 3023–3033 | language = German | doi = 10.1002/cber.189002302232| url = https://zenodo.org/record/1425592}}
• {{Cite journal | doi = 10.1002/prac.18940500125 | title = 20. Hydrazide und Azide organischer Säuren I. Abhandlung | year = 1894 | last = Curtius | first = Th. | authorlink = Theodor Curtius | journal = J. Prakt. Chem. | volume = 50 | issue = 1 | pages = 275–294 | language = German| url = https://zenodo.org/record/1427976}}
• {{cite journal | first = August | last = Darapsky | journal = J. Prakt. Chem. | volume = 146 | pages = 250–267 | year = 1936 | doi = 10.1002/prac.19361460806 | title = Darstellung von α-Aminosäuren aus Alkyl-cyanessigsäuren | language = German | issue = 8–12}}
• {{cite journal | first1 = August | last1 = Darapsky | first2 = Dietrich | last2 = Hillers | journal = J. Prakt. Chem. | volume = 92 | issue = 1 | pages = 297–341 | year = 1915 | doi = 10.1002/prac.19150920117 | title = Über das Hydrazid der Cyanessigsäure, Isonitrosocyanessigsäure und Nitrocyanessigsäure | url = https://zenodo.org/record/1428056 | language = German}}

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Category:Functional groups