Mechanism of Phosphorus–Carbon Bond Formation in the Amidoalkylation of Phosphonous Carboxylic Acids
Publication type: Journal Article
Publication date: 2020-12-22
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
33352042
Organic Chemistry
Abstract
An unusual greater reactivity of phosphonous propionic acids was found in comparison with phosphonous propionic esters in carbamate version of Kabachnik-Fields reaction. Compounds of tricoordinated phosphorus generated in situ during the amidoalkylation of hydrophosphorylic compounds in acetyl chloride/acetic anhydride mixture were found by 31P NMR analysis. A hypothesis is proposed about the generation of spirophosphoranes in situ to explain the mechanism for the formation of the phosphorus-carbon bond in the reaction under study.
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13
Total citations:
13
Citations from 2025:
2
(15.38%)
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GOST
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Dmitriev M. E. et al. Mechanism of Phosphorus–Carbon Bond Formation in the Amidoalkylation of Phosphonous Carboxylic Acids // Journal of Organic Chemistry. 2020. Vol. 86. No. 1. pp. 593-600.
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Dmitriev M. E., Golovash S. R., Borodachev A. V., Ragulin V. V. Mechanism of Phosphorus–Carbon Bond Formation in the Amidoalkylation of Phosphonous Carboxylic Acids // Journal of Organic Chemistry. 2020. Vol. 86. No. 1. pp. 593-600.
Cite this
RIS
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TY - JOUR
DO - 10.1021/acs.joc.0c02259
UR - https://doi.org/10.1021/acs.joc.0c02259
TI - Mechanism of Phosphorus–Carbon Bond Formation in the Amidoalkylation of Phosphonous Carboxylic Acids
T2 - Journal of Organic Chemistry
AU - Dmitriev, Maxim E
AU - Golovash, Sofia R
AU - Borodachev, Alexei V
AU - Ragulin, V V
PY - 2020
DA - 2020/12/22
PB - American Chemical Society (ACS)
SP - 593-600
IS - 1
VL - 86
PMID - 33352042
SN - 0022-3263
SN - 1520-6904
ER -
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BibTex (up to 50 authors)
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@article{2020_Dmitriev,
author = {Maxim E Dmitriev and Sofia R Golovash and Alexei V Borodachev and V V Ragulin},
title = {Mechanism of Phosphorus–Carbon Bond Formation in the Amidoalkylation of Phosphonous Carboxylic Acids},
journal = {Journal of Organic Chemistry},
year = {2020},
volume = {86},
publisher = {American Chemical Society (ACS)},
month = {dec},
url = {https://doi.org/10.1021/acs.joc.0c02259},
number = {1},
pages = {593--600},
doi = {10.1021/acs.joc.0c02259}
}
Cite this
MLA
Copy
Dmitriev, Maxim E., et al. “Mechanism of Phosphorus–Carbon Bond Formation in the Amidoalkylation of Phosphonous Carboxylic Acids.” Journal of Organic Chemistry, vol. 86, no. 1, Dec. 2020, pp. 593-600. https://doi.org/10.1021/acs.joc.0c02259.