酰基叠氮

酰基叠氮是一类羧酸衍生物,通式 RCON3

酰基叠氮的结构

制备

酰氯叠氮化钠反应,产生酰基叠氮。[1][2]

 

它们也可以由叠氮化钠和羧酸在三苯基膦三氯乙腈催化剂的存在下反应而成。[3]另一条制备路线是叠氮化碘反应,后者由叠氮化钠和一氯化碘在乙腈中形成。[4]

用处

酰基叠氮是化学试剂。在库尔提斯重排反应中,酰基叠氮分解成异氰酸酯[5][6][7][8]

 

酰基叠氮也用于Darapasky递降反应中。[9][10][11][12][13]

 

参见

  • 碳酰叠氮是酰基叠氮的R也是叠氮基而成的化合物。

参考资料

  1. ^ (1944) "Undecyl isocyanate". Org. Synth. 24: 94; Coll. Vol. 3: 846. 
  2. ^ Munch-Petersen, Jon (1953). "m-Nitrobenzazide (Benzoyl azide, m-nitro-)". Org. Synth. 33: 53; Coll. Vol. 4: 715. 
  3. ^ Jang, Doo; Kim, Joong-Gon. Direct Synthesis of Acyl Azides from Carboxylic Acids by the Combination of Trichloroacetonitrile, Triphenylphosphine and Sodium Azide. Synlett. 2008, 2008 (13): 2072–2074. doi:10.1055/s-2008-1077979. 
  4. ^ Marinescu, Lavinia; Thinggaard, Jacob; Thomsen, Ib B.; Bols, Mikael. Radical Azidonation of Aldehydes. J. Org. Chem. 2003, 68 (24): 9453–9455. PMID 14629171. doi:10.1021/jo035163v. 
  5. ^ Curtius, Th. Ueber Stickstoffwasserstoffsäure (Azoimid) N3H. Ber. 1890, 23 (2): 3023–3033 [2021-07-11]. doi:10.1002/cber.189002302232. (原始内容存档于2021-07-14) (德语). 
  6. ^ Curtius, Th. 20. Hydrazide und Azide organischer Säuren I. Abhandlung. J. Prakt. Chem. 1894, 50 (1): 275–294 [2021-07-11]. doi:10.1002/prac.18940500125. (原始内容存档于2022-06-30) (德语). 
  7. ^ Smith, Peter A. S. The Curtius reaction. Org. React. 1946, 3: 337–449. ISBN 0471264180. doi:10.1002/0471264180.or003.09. 
  8. ^ Scriven, Eric F. V.; Turnbull, Kenneth. Azides: Their preparation and synthetic uses. Chem. Rev. 1988, 88 (2): 297–368. doi:10.1021/cr00084a001. 
  9. ^ Darapsky, August. Darstellung von α-Aminosäuren aus Alkyl-cyanessigsäuren. J. Prakt. Chem. 1936, 146 (8–12): 250–267. doi:10.1002/prac.19361460806 (德语). 
  10. ^ Darapsky, August; Hillers, Dietrich. Über das Hydrazid der Cyanessigsäure, Isonitrosocyanessigsäure und Nitrocyanessigsäure. J. Prakt. Chem. 1915, 92 (1): 297–341 [2021-07-11]. doi:10.1002/prac.19150920117. (原始内容存档于2021-07-12) (德语). 
  11. ^ Gagnon, Paul E.; Boivin, Paul A.; Craig, Hugh M. Synthesis of Amino Acids from Substituted Cyanoacetic Esters. Can. J. Chem. 1951, 29 (1): 70–75. doi:10.1139/v51-009. 
  12. ^ E. H. Rodd. Chemistry of Carbon Compounds 2nd. New York: 1157. 1965. 
  13. ^ Gagnon, Paul E.; Nadeau, Guy; Côté, Raymond. Synthesis of α-Amino Acids from Ethyl Cyanoacetate. Can. J. Chem. 1952, 30 (8): 592–597. doi:10.1139/v52-071.