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
2.
Gibson S., Rudd M.
Advanced Synthesis and Catalysis,
2007
3.
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
6.
Alguacil F.J., Alonso M.
Hydrometallurgy,
2004
7.
Flett D.S.
Journal of Organometallic Chemistry,
2005
8.
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.
Liu H., Owen J.S., Alivisatos A.P.
Journal of the American Chemical Society,
2006
13.
Henkes A.E., Vasquez Y., Schaak R.E.
Journal of the American Chemical Society,
2007
14.
Marklund A., Andersson B., Haglund P.
Environmental Science & Technology,
2005
15.
Faghihi K., Zamani K.
Journal of Applied Polymer Science,
2006
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
19.
Bader A., Lindner E.
Coordination Chemistry Reviews,
1991
20.
Lindner E., Pautz S., Haustein M.
Coordination Chemistry Reviews,
1996
21.
Lindner E., Pautz S., Fawzi R., Steimann M.
Organometallics,
1998
22.
E. Lindner, D.O.S. 3736722, 1989. (Chem. Abstr., 1990, 112, 20680f).
23.
Das P., Sharma M., Kumari N., Konwar D., Dutta D.K.
Applied Organometallic Chemistry,
2002
24.
Le Gall I., Laurent P., Soulier E., Salaün J., des Abbayes H.
Journal of Organometallic Chemistry,
1998
25.
Lindner E., Meyer S., Wegner P., Karle B., Sickinger A., Steger B.
Journal of Organometallic Chemistry,
1987
26.
Werner H., Hampp A., Windmüller B.
Journal of Organometallic Chemistry,
1992
27.
Arbuzova S.N., Gusarova N.K., Trofimov B.A.
Arkivoc,
2006
28.
Trofimov B.A., Gusarova N.K.
Mendeleev Communications,
2009
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.
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.
RAUHUT M.M., CURRIER H.A., SEMSEL A.M., WYSTRACH V.P.
Journal of Organic Chemistry,
1961