title: A Fresh Look at the Staudinger Reaction on Azido Esters: Formation of 2H-1,2,3-Triazol-4-ols from α-Azido Esters Using Trialkyl Phosphines.
abstract: Phenyl esters of α-azido acids react with trialkylphosphines in THF/H2O to give 5-substituted 2H-1,2,3-triazol-4-ols in good to excellent yields. In contrast, their reaction with PPh3 in THF/H2O give the amino esters as the major product and no triazoles. Reaction between an α-azido phenyl ester and P(OEt)3 provided the corresponding phosphoramidate in excellent yield, but no triazole was formed.
authors.affiliation: Department of Chemistry, University of Waterloo , 200 University Avenue West, Waterloo, Ontario Canada , N2L 3G1.
authors.forename: Scott D
authors.initials: SD
authors.lastname: Taylor
authors.affiliation: Department of Chemistry, University of Waterloo , 200 University Avenue West, Waterloo, Ontario Canada , N2L 3G1.
authors.forename: Chuda Raj
authors.initials: CR
authors.lastname: Lohani