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The surprising diacylation of diethyl (ethoxycarbonylmethyl)phosphonate

Kinga V Gulyás 1
Kinga V Gulyás
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10.1016/j.mencom.2021.03.033
Published 2021-03-03
Communication , Volume 31, Issue 2, 244-245
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Gulyás K. V., Keglevich G. T. The surprising diacylation of diethyl (ethoxycarbonylmethyl)phosphonate // Mendeleev Communications. 2021. Vol. 31. No. 2. pp. 244-245.
GOST all authors (up to 50) Copy
Gulyás K. V., Keglevich G. T. The surprising diacylation of diethyl (ethoxycarbonylmethyl)phosphonate // Mendeleev Communications. 2021. Vol. 31. No. 2. pp. 244-245.
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TY - JOUR
DO - 10.1016/j.mencom.2021.03.033
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.03.033
TI - The surprising diacylation of diethyl (ethoxycarbonylmethyl)phosphonate
T2 - Mendeleev Communications
AU - Gulyás, Kinga V
AU - Keglevich, György Tibor
PY - 2021
DA - 2021/03/03
PB - Mendeleev Communications
SP - 244-245
IS - 2
VL - 31
ER -
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@article{2021_Gulyás,
author = {Kinga V Gulyás and György Tibor Keglevich},
title = {The surprising diacylation of diethyl (ethoxycarbonylmethyl)phosphonate},
journal = {Mendeleev Communications},
year = {2021},
volume = {31},
publisher = {Mendeleev Communications},
month = {Mar},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.03.033},
number = {2},
pages = {244--245},
doi = {10.1016/j.mencom.2021.03.033}
}
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Gulyás, Kinga V., and György Tibor Keglevich. “The surprising diacylation of diethyl (ethoxycarbonylmethyl)phosphonate.” Mendeleev Communications, vol. 31, no. 2, Mar. 2021, pp. 244-245. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.03.033.

Keywords

acylation
CH-acidic compounds
diacylation
phosphonates
relative DpKa value

Abstract

Deprotonation of diethyl (ethoxycarbonylmethyl)-phosphonate with NaH followed by treatment with acyl chlorides affords surprisingly the corresponding C,C-diacylated derivatives as the predominating products.

References

5.
On A Safe and Practical Method for The Preparation of β-Keto Phosphonates1
Corbel B., L'Hostis-Kervella I., Haelters J.
Synthetic Communications, 1996
6.
448. A new synthesis of acetylenes. Part I
Gough S.T., Trippett S.
Journal of the Chemical Society (Resumed), 1962
7.
10.1016/j.mencom.2021.03.033_bib0035
Cahiez
e-EROS Encyclopedia of Reagents for Organic Synthesis, 2001
8.
Some observations on the Wadsworth–Emmons olefination reaction
Durrant G., Sutherland J.K.
Journal of the Chemical Society Perkin Transactions 1, 1972
9.
10.1016/j.mencom.2021.03.033_bib0045
Sakhibullina
Zh. Obshch. Khim., 1982
10.
Reactions of Phosphorus Compounds. I. Diethyl Carbamoylmethylphosphonates
SPEZIALE A.J., FREEMAN R.C.
Journal of Organic Chemistry, 1958
12.
10.1016/j.mencom.2021.03.033_bib0060
Frisch
Gaussian 16, Revision C. 01, 2016