CYCLOADDITION OF METHYLAZIDE ON ALKENES B EARING 2 GEMINATE ELECTRON-WITHDRAWING GROUPS - THERMAL-STABILITY OF OBTAINED 1,2,3-TRIAZOLINES

Authors
LEHETET G DANIONBOUGOT R CARRIE R
Citation
G. Lehetet et al., CYCLOADDITION OF METHYLAZIDE ON ALKENES B EARING 2 GEMINATE ELECTRON-WITHDRAWING GROUPS - THERMAL-STABILITY OF OBTAINED 1,2,3-TRIAZOLINES, Bulletin des Societes chimiques belges, 105(5), 1996, pp. 259-272
Citations number
32
Categorie Soggetti
Chemistry
Journal title
Bulletin des Societes chimiques belges → ACNP
ISSN journal
00379646
Volume
105
Issue
5
Year of publication
1996
Pages
259 - 272
Database
ISI
SICI code
0037-9646(1996)105:5<259:COMOAB>2.0.ZU;2-W
Abstract
Methylazide reacts with alkenes bearing two electron-withdrawing subst ituents on the same sp(2) carbone and leads to corresponding 1,2,3-tri azolines with these substituents in 4 position. Thermolysis of these 1 ,2,3-triazolines give cycloreversion (alkene + methylazide) and azirid ines after extrusion of nitrogen. In the conditions of the thermolysis , aziridine carbone-carbone bond breaks, leading to azomethine ylids t hat are trapped with alkenes and give pyrrolidines.