Formation of azomethine ylids by thermolysis of oxazolidines. Study of the reaction in solution and in the gaseous phase
Thermolysis of oxazolidines leads to azomethine ylids via cycloreversion.In the liquid phase, these intermediates then give 1-3 dipolar cycloaddition; in the gaseous phase, they lead to aziridines.With an alkyl group in position 2, we observed also the formation of enamines.The effect of substituents on both the cycloreversion reaction and the evolution of azomethine ylids was studied.The mechanism of the process tautomerism aziridine -> azomethine ylid -> enamine is discussed.Keywords - azomethine ylids / oxazolidines / cycloreversion / aziridines / enamines / tautomerism
Bureau, R.,Mortier, J.,Joucla, M.
p. 584 - 596
(2007/10/02)
FLASH VACUUM THERMOLYSIS OF OXAZOLIDINES : A NEW WAY TO REACTIVE AZOMETHINE YLIDES. RING CLOSURE TO AZIRIDINES.
Flash vacuum thermolysis of oxazolidines leads to azomethine ylides which undergo ring closure to aziridines.
Joucla, Marc,Mortier, Jacques,Bureau, Ronan
p. 2975 - 2976
(2007/10/02)
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