醯基疊氮

醯基疊氮是一類羧酸衍生物,通式 RCON3

醯基疊氮的結構

製備

醯氯疊氮化鈉反應,產生醯基疊氮。[1][2]

 

它們也可以由疊氮化鈉和羧酸在三苯基膦三氯乙腈催化劑的存在下反應而成。[3]另一條製備路線是疊氮化碘反應,後者由疊氮化鈉和一氯化碘在乙腈中形成。[4]

用處

醯基疊氮是化學試劑。在庫爾提斯重排反應中,醯基疊氮分解成異氰酸酯[5][6][7][8]

 

醯基疊氮也用於Darapasky遞降反應中。[9][10][11][12][13]

 

參見

  • 碳醯疊氮是醯基疊氮的R也是疊氮基而成的化合物。

參考資料

  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. (原始內容存檔於2021-07-14) (德語). 
  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. (原始內容存檔於2022-06-30) (德語). 
  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 (德語). 
  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. (原始內容存檔於2021-07-12) (德語). 
  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.