DECOMPOSITION OF ARYLAZIDES BY THF/n-BUTYLLITHIUM-II- -ISOLATION OF 1-ARYL-4,5-DIHYDRO-5-HYDROXY-1H-1,2,3-TRIAZOLES

Article abstract of DOI:10.1016/S0040-4020(01)87546-3

By reaction of arylazides having no electron-withdrawing groups with the enolate ion of the acetaldehyde (formed by cycloreversion of THF in the presence of n-buthyllithium), 1-aryl-4,5-dihydro-5-hydroxy-1H-1,2,3-triazoles could be isolated and then characterized.Further reaction of such hydroxytriazolines with the same enolate ion afforded substantial amounts of the corresponding N-formylanilines , confirming their intermediacy in the previously reported decomposition of arylazides by THF/n-butyllithium.On the other hand, using alkoxides as bases, the preferred scheme of conversion of the hydroxytriazolines was found to be the known dehydration to 1-aryl-1H-1,2,3-triazoles.