ol6b02204_si_002.cif (157.23 kB)
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
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posted on 2016-08-17, 20:30 authored by Scott D. Taylor, Chuda Raj LohaniPhenyl
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.
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