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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

Scott D. Taylor* and Chuda Raj Lohani

*Department of Chemistry, University of Waterloo, 200 University Avenue West, Waterloo, Ontario Canada, N2L 3G1, Email: s5tayloruwaterloo.ca

S. D. Taylor, C. R. Lohani, Org. Lett., 2016, 18, 4412-4415.

DOI: 10.1021/acs.orglett.6b02204 (free Supporting Information)


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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 very good yields, whereas their reaction with PPh3 provides amino esters as the major product and no triazoles.

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Key Words

1,2,3-triazoles


ID: J54-Y2016