Synthesis of carbamoyl azides from primary amines and carbon dioxide under mild conditions.
Treatment of amines under a carbon dioxide atmosphere with tetramethylphenylguanidine (PhTMG) and diphenylphosphoryl azide (DPPA) in acetonitrile below 0 degrees C provides carbamoyl azides in high to excellent yields. In addition, epimerization is not observed when optically pure alpha-amino esters are used as substrates.
García-Egido
Eduardo
E
Departamento de Química OrgAnica, Universidade de Vigo, E-36310 Vigo, Spain.
Fernandez-Suarez
Miryam
M
Muñoz
Luis
L
D000588:Amines / Q000737:chemistry*; D001386:Azides / Q000138:chemical synthesis* / Q000737:chemistry; D002245:Carbon Dioxide / Q000737:chemistry*; D015394:Molecular Structure; D013696:Temperature
D000588:Amines; D001386:Azides; D002245:Carbon Dioxide