Home / Publications / Free-radical addition of phosphine to vinyl ethers: atom-economic synthesis of tris(2-organyloxyethyl)phosphines and their derivatives

Free-radical addition of phosphine to vinyl ethers: atom-economic synthesis of tris(2-organyloxyethyl)phosphines and their derivatives

Nina Kuzminichna Gusarova 1
Nina Kuzminichna Gusarova
Svetlana Il'yasovna Verkhoturova 1
Svetlana Il'yasovna Verkhoturova
Tatyana Ivanovna Kazantseva 1
Tatyana Ivanovna Kazantseva
Valentina L'vovna Mikhailenko 1
Valentina L'vovna Mikhailenko
Svetlana Nikolaevna Arbuzova 1
Svetlana Nikolaevna Arbuzova
Boris Aleksandrovich Trofimov 1
Boris Aleksandrovich Trofimov
Published 2011-01-12
CommunicationVolume 21, Issue 1, 17-18
10
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Gusarova N. K. et al. Free-radical addition of phosphine to vinyl ethers: atom-economic synthesis of tris(2-organyloxyethyl)phosphines and their derivatives // Mendeleev Communications. 2011. Vol. 21. No. 1. pp. 17-18.
GOST all authors (up to 50) Copy
Gusarova N. K., Verkhoturova S. I., Kazantseva T. I., Mikhailenko V. L., Arbuzova S. N., Trofimov B. A. Free-radical addition of phosphine to vinyl ethers: atom-economic synthesis of tris(2-organyloxyethyl)phosphines and their derivatives // Mendeleev Communications. 2011. Vol. 21. No. 1. pp. 17-18.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2011.01.007
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2011.01.007
TI - Free-radical addition of phosphine to vinyl ethers: atom-economic synthesis of tris(2-organyloxyethyl)phosphines and their derivatives
T2 - Mendeleev Communications
AU - Gusarova, Nina Kuzminichna
AU - Verkhoturova, Svetlana Il'yasovna
AU - Kazantseva, Tatyana Ivanovna
AU - Mikhailenko, Valentina L'vovna
AU - Arbuzova, Svetlana Nikolaevna
AU - Trofimov, Boris Aleksandrovich
PY - 2011
DA - 2011/01/12
PB - Mendeleev Communications
SP - 17-18
IS - 1
VL - 21
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2011_Gusarova,
author = {Nina Kuzminichna Gusarova and Svetlana Il'yasovna Verkhoturova and Tatyana Ivanovna Kazantseva and Valentina L'vovna Mikhailenko and Svetlana Nikolaevna Arbuzova and Boris Aleksandrovich Trofimov},
title = {Free-radical addition of phosphine to vinyl ethers: atom-economic synthesis of tris(2-organyloxyethyl)phosphines and their derivatives},
journal = {Mendeleev Communications},
year = {2011},
volume = {21},
publisher = {Mendeleev Communications},
month = {Jan},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2011.01.007},
number = {1},
pages = {17--18},
doi = {10.1016/j.mencom.2011.01.007}
}
MLA
Cite this
MLA Copy
Gusarova, Nina Kuzminichna, et al. “Free-radical addition of phosphine to vinyl ethers: atom-economic synthesis of tris(2-organyloxyethyl)phosphines and their derivatives.” Mendeleev Communications, vol. 21, no. 1, Jan. 2011, pp. 17-18. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2011.01.007.

Abstract

Phosphine, generated from red phosphorus in the system KOH–H2O–toluene, reacts with vinyl ethers under radical initiation (AIBN, dioxane, 78–80°C, atmospheric pressure) to give tris(2-organyloxyethyl)phosphines, which are transformed to the corresponding phosphine chalcogenides (in up to 73% isolated yield) via the reactions with air oxygen, elemental sulfur or selenium.

References

1.
10.1016/j.mencom.2011.01.007_bib0005_1
Whittlesey
Organometallic Chemistry, 2000
3.
Modular Synthesis of ChiraClick Ligands:  A Library of P-Chirogenic Phosphines
Dolhem F., Johansson M.J., Antonsson T., Kann N.
Journal of Combinatorial Chemistry, 2007
4.
Phosphorus Ligands in Asymmetric Catalysis: Synthesis and Applications, ed. A. Bërner, Wiley-VCH, New York, 2008.
5.
Trofimov B.A., Vasilevsky S.F., Gusarova N.K., Malysheva S.F., Baranov D.S., Mamatyuk V.I., Gatilov Y.V.
Mendeleev Communications, 2008
8.
Uranium(VI) extraction by Winsor II microemulsion systems using trialkyl phosphine oxide
Shan Z., Yan-zhao Y., Tao Z., Jian H., Chang-Hong L.
Journal of Radioanalytical and Nuclear Chemistry, 2005
9.
10.1016/j.mencom.2011.01.007_bib0010_4
Men'shikov
Zh. Prikl. Khim., 2009
10.
The Chemistry of Nanomaterials, eds. C. N. R. Rao, A. Müller and A. K. Cheetham, Wiley-VCH, New York, 2004, vol. 2.
11.
10.1016/j.mencom.2011.01.007_bib0015_2
Gubin
Izv. Akad. Nauk, Ser. Khim., 2005
12.
Mechanistic Study of Precursor Evolution in Colloidal Group II−VI Semiconductor Nanocrystal Synthesis
Liu H., Owen J.S., Alivisatos A.P.
Journal of the American Chemical Society, 2006
13.
Converting Metals into Phosphides:  A General Strategy for the Synthesis of Metal Phosphide Nanocrystals
Henkes A.E., Vasquez Y., Schaak R.E.
Journal of the American Chemical Society, 2007
14.
Organophosphorus Flame Retardants and Plasticizers in Swedish Sewage Treatment Plants
Marklund A., Andersson B., Haglund P.
Environmental Science & Technology, 2005
16.
10.1016/j.mencom.2011.01.007_bib0020_3
Plotnikova
Zh. Prikl. Khim., 2008
17.
10.1016/j.mencom.2011.01.007_bib0025_1
Engel
Synthesis of Carbon–Phosphorus Bonds, 2003
18.
10.1016/j.mencom.2011.01.007_bib0025_2
Murphy
Organophosphorus Reagents: A Practical Approach in Chemistry, 2004
22.
E. Lindner, D.O.S. 3736722, 1989. (Chem. Abstr., 1990, 112, 20680f).
23.
Rhodium(I) carbonyl complexes of ether-phosphine ligands and their reactivity
Das P., Sharma M., Kumari N., Konwar D., Dutta D.K.
Applied Organometallic Chemistry, 2002
24.
COMPLEXATION ON RHODIUM OF BIDENTATE AND POTENTIALLY HEMILABILE PHOSPHOROUS LIGANDS
Le Gall I., Laurent P., Soulier E., Salaün J., des Abbayes H.
Journal of Organometallic Chemistry, 1998
29.
Gusarova N.K., Ivanova N.I., Bogdanova M.V., Malysheva S.F., Belogorlova N.A., Sukhov B.G., Trofimov B.A.
Mendeleev Communications, 2004
30.
Facile Synthesis of Hyper-Branched Tetraphosphanes and Tetraphosphane Chalcogenides
Trofimov B.A., Malysheva S.F., Belogorlova N.A., Kuimov V.A., Albanov A.I., Gusarova N.K.
European Journal of Organic Chemistry, 2009
31.
10.1016/j.mencom.2011.01.007_bib0060_3
Oparina
Synthesis, 2009
32.
Gusarova N.K., Malysheva S.F., Oparina L.A., Belogorlova N.A., Tantsyrev A.P., Parshina L.N., Sukhov B.G., Tlegenov R.T., Trofimov B.A.
Arkivoc, 2009
33.
Gusarova N.K., Malysheva S.F., Kuimov V.A., Belogorlova N.A., Mikhailenko V.L., Trofimov B.A.
Mendeleev Communications, 2008
34.
The Free Radical Addition of Phosphines to Unsaturated Compounds
RAUHUT M.M., CURRIER H.A., SEMSEL A.M., WYSTRACH V.P.
Journal of Organic Chemistry, 1961