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
Publication type: Journal Article
Publication date: 2016-08-17
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
27532326
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
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.
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Total citations:
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Citations from 2024:
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Taylor S. D., Lohani C. R. 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 // Organic Letters. 2016. Vol. 18. No. 17. pp. 4412-4415.
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Taylor S. D., Lohani C. R. 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 // Organic Letters. 2016. Vol. 18. No. 17. pp. 4412-4415.
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RIS
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TY - JOUR
DO - 10.1021/acs.orglett.6b02204
UR - https://doi.org/10.1021/acs.orglett.6b02204
TI - 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
T2 - Organic Letters
AU - Taylor, Scott D
AU - Lohani, Chuda Raj
PY - 2016
DA - 2016/08/17
PB - American Chemical Society (ACS)
SP - 4412-4415
IS - 17
VL - 18
PMID - 27532326
SN - 1523-7060
SN - 1523-7052
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2016_Taylor,
author = {Scott D Taylor and Chuda Raj Lohani},
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},
journal = {Organic Letters},
year = {2016},
volume = {18},
publisher = {American Chemical Society (ACS)},
month = {aug},
url = {https://doi.org/10.1021/acs.orglett.6b02204},
number = {17},
pages = {4412--4415},
doi = {10.1021/acs.orglett.6b02204}
}
Cite this
MLA
Copy
Taylor, Scott D., and Chuda Raj Lohani. “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.” Organic Letters, vol. 18, no. 17, Aug. 2016, pp. 4412-4415. https://doi.org/10.1021/acs.orglett.6b02204.