Home / Publications / Single-stage synthesis of alkyl-H-phosphinic acids from elemental phosphorus and alkyl bromides

Single-stage synthesis of alkyl-H-phosphinic acids from elemental phosphorus and alkyl bromides

Nina Kuzminichna Gusarova 1
Nina Kuzminichna Gusarova
Anastasiya Olegovna Sutyrina 1
Anastasiya Olegovna Sutyrina
Vladimir Anatol'evich Kuimov 1
Vladimir Anatol'evich Kuimov
Svetlana Filippovna Malysheva 1
Svetlana Filippovna Malysheva
Natalia Alekseevna Belogorlova 1
Natalia Alekseevna Belogorlova
Pavel Anatol'evich Volkov 1
Pavel Anatol'evich Volkov
Boris Aleksandrovich Trofimov 1
Boris Aleksandrovich Trofimov
Published 2019-04-26
CommunicationVolume 29, Issue 3, 328-330
11
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Gusarova N. K. et al. Single-stage synthesis of alkyl-H-phosphinic acids from elemental phosphorus and alkyl bromides // Mendeleev Communications. 2019. Vol. 29. No. 3. pp. 328-330.
GOST all authors (up to 50) Copy
Gusarova N. K., Sutyrina A. O., Kuimov V. A., Malysheva S. F., Belogorlova N. A., Volkov P. A., Trofimov B. A. Single-stage synthesis of alkyl-H-phosphinic acids from elemental phosphorus and alkyl bromides // Mendeleev Communications. 2019. Vol. 29. No. 3. pp. 328-330.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2019.05.030
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2019.05.030
TI - Single-stage synthesis of alkyl-H-phosphinic acids from elemental phosphorus and alkyl bromides
T2 - Mendeleev Communications
AU - Gusarova, Nina Kuzminichna
AU - Sutyrina, Anastasiya Olegovna
AU - Kuimov, Vladimir Anatol'evich
AU - Malysheva, Svetlana Filippovna
AU - Belogorlova, Natalia Alekseevna
AU - Volkov, Pavel Anatol'evich
AU - Trofimov, Boris Aleksandrovich
PY - 2019
DA - 2019/04/26
PB - Mendeleev Communications
SP - 328-330
IS - 3
VL - 29
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2019_Gusarova,
author = {Nina Kuzminichna Gusarova and Anastasiya Olegovna Sutyrina and Vladimir Anatol'evich Kuimov and Svetlana Filippovna Malysheva and Natalia Alekseevna Belogorlova and Pavel Anatol'evich Volkov and Boris Aleksandrovich Trofimov},
title = {Single-stage synthesis of alkyl-H-phosphinic acids from elemental phosphorus and alkyl bromides},
journal = {Mendeleev Communications},
year = {2019},
volume = {29},
publisher = {Mendeleev Communications},
month = {Apr},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2019.05.030},
number = {3},
pages = {328--330},
doi = {10.1016/j.mencom.2019.05.030}
}
MLA
Cite this
MLA Copy
Gusarova, Nina Kuzminichna, et al. “Single-stage synthesis of alkyl-H-phosphinic acids from elemental phosphorus and alkyl bromides.” Mendeleev Communications, vol. 29, no. 3, Apr. 2019, pp. 328-330. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2019.05.030.

Abstract

Elemental phosphorus (red or white) reacts with alkyl bromides at 60–62°C in the phase-transfer catalytic system KOH/H2O/PhMe/Et3BnNCl to afford alkyl-H-phosphinic acids in up to 47% yield.

References

1.
Structural Diversity in Zinc Phosphates and Phosphinates: Observation of a Lattice Water Dimer Sandwiched Between Phosphoryl Oxygen Atoms
Pothiraja R., Shanmugan S., Walawalkar M.G., Nethaji M., Butcher R.J., Murugavel R.
European Journal of Inorganic Chemistry, 2008
2.
S. Luo, K.M. Macauley and J. T. Poulton, Patent EP 2075266, 2009.
3.
New dinuclear nickel(II) complexes: synthesis, structure, electrochemical, and magnetic properties.
Yakhvarov D., Trofimova E., Sinyashin O., Kataeva O., Budnikova Y., Lönnecke P., Hey-Hawkins E., Petr A., Krupskaya Y., Kataev V., Klingeler R., Büchner B.
Inorganic Chemistry, 2011
4.
Trofimova E.A., Dobrynin A.B., Gerasimova T.P., Katsyuba S.A., Sinyashin O.G., Yakhvarov D.G.
Mendeleev Communications, 2013
5.
10.1016/j.mencom.2019.05.030_sbref0005e
Trofimova
Butlerovskie Soobshcheniya, 2013
6.
Yakhvarov D.G., Trofimova E.A., Dobrynin A.B., Gerasimova T.P., Katsyuba S.A., Sinyashin O.G.
Mendeleev Communications, 2015
7.
Phosphinic Acid Analogs of GABA. 1. New Potent and Selective GABAB Agonists
Froestl W., Mickel S.J., Hall R.G., von Sprecher G., Strub D., Baumann P.A., Brugger F., Gentsch C., Jaekel J.
Journal of Medicinal Chemistry, 1995
8.
Phosphinic Acid Analogs of GABA. 2. Selective, Orally Active GABAB Antagonists
Froestl W., Mickel S.J., von Sprecher G., Diel P.J., Hall R.G., Maier L., Strub D., Melillo V., Baumann P.A.
Journal of Medicinal Chemistry, 1995
9.
Vinyukov A.V., Borodachev A.V., Starikov A.S., Afanasyev A.V., Dmitriev M.E., Lednev B.V., Ragulin V.V.
Mendeleev Communications, 2018
11.
R. Du, J. Xu, Q. Cheng, S. Yuan, L. Wang and T. Guo, Patent WO 2014101346 A1, 2014.
12.
E.S. Ermolaev, PhD Thesis, Kazan, 2008.
14.
10.1016/j.mencom.2019.05.030_sbref0030a
Ebetino
Elem., 2002
15.
A useful synthesis of the Phe-Arg phosphinic acid dipeptide isostere
Kende A.S., Dong H., Liu X., Ebetino F.H.
Tetrahedron Letters, 2002
19.
Kiss N.Z., Rádai Z., Tihanyi I., Szabó T., Keglevich G.
Mendeleev Communications, 2018
20.
Progresses in the Field of Drug Design to Combat Tropical Protozoan Parasitic Diseases
Linares G., Ravaschino E., Rodriguez J.
Current Medicinal Chemistry, 2006
21.
Phosphonic acid: preparation and applications
Sevrain C.M., Berchel M., Couthon H., Jaffrès P.
Beilstein Journal of Organic Chemistry, 2017
23.
?,?-Difluoro-H-phosphinates: Useful Intermediates for a Variety of Phosphate Isosteres
Gautier A., Garipova G., Salcedo C., Balieu S., Piettre S.R.
Angewandte Chemie - International Edition, 2004
29.
10.1016/j.mencom.2019.05.030_sbref0050a
Greenwood
Chemistry of the Elements, 1997
30.
10.1016/j.mencom.2019.05.030_sbref0050b
Corbridge
Phosphorus: Chemistry, Biochemistry and Technology, 2013
34.
10.1016/j.mencom.2019.05.030_sbref0055d
Virieux
2015
35.
Palladium-Catalyzed Hydrophosphinylation of Alkenes and Alkynes
Deprèle S., Montchamp J.
Journal of the American Chemical Society, 2002
38.
10.1016/j.mencom.2019.05.030_sbref0065b
Troev
Reactivity of P–H Group of Phosphorus Based Compounds, 2018
39.
10.1016/j.mencom.2019.05.030_sbref0070a
Gusarova
Zh. Obshch. Khim., 1990
40.
10.1016/j.mencom.2019.05.030_sbref0070b
Malysheva
Russ. J. Gen. Chem., 1997
41.
Preconcentration of gold, silver, palladium, platinum, and ruthenium with organophosphorus extractants
Men’shikov V.I., Voronova I.Y., Proidakova O.A., Malysheva S.F., Ivanova N.I., Belogorlova N.A., Gusarova N.K., Trofimov B.A.
Russian Journal of Applied Chemistry, 2009
42.
Supercritical fluid extraction of uranium and thorium from nitric acid medium using organophosphorous compounds
Pitchaiah K. ., Sujatha K., Brahmmananda Rao C. ., Subramaniam S., Sivaraman N., Vasudeva Rao P. .
Radiochimica Acta, 2014
43.
Ligands for f-element extraction used in the nuclear fuel cycle
Leoncini A., Huskens J., Verboom W.
Chemical Society Reviews, 2017