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Phosphorus halide free synthesis of 1,2,3,4-tetrahydroisophosphinoline 2-oxides

Svetlana Filippovna Malysheva 1
Svetlana Filippovna Malysheva
, 
Nina Kuzminichna Gusarova 1
Nina Kuzminichna Gusarova
, 
Natalia Alekseevna Belogorlova 1
Natalia Alekseevna Belogorlova
, 
Anastasiya Olegovna Sutyrina 1
Anastasiya Olegovna Sutyrina
, 
Alexander Ivanovich Albanov 1
Alexander Ivanovich Albanov
, 
Boris Genad'evch Sukhov 1
Boris Genad'evch Sukhov
, 
Vladimir Anatol'evich Kuimov 1
Vladimir Anatol'evich Kuimov
, 
Yuriy Igorevich Litvintsev 1
Yuriy Igorevich Litvintsev
, 
Boris Aleksandrovich Trofimov 1
Boris Aleksandrovich Trofimov
10.1016/j.mencom.2018.01.008
Published 2017-12-22
Communication , Volume 28, Issue 1, 29-30
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Malysheva S. F. et al. Phosphorus halide free synthesis of 1,2,3,4-tetrahydroisophosphinoline 2-oxides // Mendeleev Communications. 2017. Vol. 28. No. 1. pp. 29-30.
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Malysheva S. F., Gusarova N. K., Belogorlova N. A., Sutyrina A. O., Albanov A. I., Sukhov B. G., Kuimov V. A., Litvintsev Y. I., Trofimov B. A. Phosphorus halide free synthesis of 1,2,3,4-tetrahydroisophosphinoline 2-oxides // Mendeleev Communications. 2017. Vol. 28. No. 1. pp. 29-30.
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TY - JOUR
DO - 10.1016/j.mencom.2018.01.008
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2018.01.008
TI - Phosphorus halide free synthesis of 1,2,3,4-tetrahydroisophosphinoline 2-oxides
T2 - Mendeleev Communications
AU - Malysheva, Svetlana Filippovna
AU - Gusarova, Nina Kuzminichna
AU - Belogorlova, Natalia Alekseevna
AU - Sutyrina, Anastasiya Olegovna
AU - Albanov, Alexander Ivanovich
AU - Sukhov, Boris Genad'evch
AU - Kuimov, Vladimir Anatol'evich
AU - Litvintsev, Yuriy Igorevich
AU - Trofimov, Boris Aleksandrovich
PY - 2017
DA - 2017/12/22
PB - Mendeleev Communications
SP - 29-30
IS - 1
VL - 28
ER -
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@article{2017_Malysheva,
author = {Svetlana Filippovna Malysheva and Nina Kuzminichna Gusarova and Natalia Alekseevna Belogorlova and Anastasiya Olegovna Sutyrina and Alexander Ivanovich Albanov and Boris Genad'evch Sukhov and Vladimir Anatol'evich Kuimov and Yuriy Igorevich Litvintsev and Boris Aleksandrovich Trofimov},
title = {Phosphorus halide free synthesis of 1,2,3,4-tetrahydroisophosphinoline 2-oxides},
journal = {Mendeleev Communications},
year = {2017},
volume = {28},
publisher = {Mendeleev Communications},
month = {Dec},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2018.01.008},
number = {1},
pages = {29--30},
doi = {10.1016/j.mencom.2018.01.008}
}
MLA
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MLA Copy
Malysheva, Svetlana Filippovna, et al. “Phosphorus halide free synthesis of 1,2,3,4-tetrahydroisophosphinoline 2-oxides.” Mendeleev Communications, vol. 28, no. 1, Dec. 2017, pp. 29-30. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2018.01.008.

Abstract

The herein developed phosphorus halide free synthesis of 1,2,3,4-tetrahydroisophosphinoline 2-oxides involves intramolecular heterocyclization of P,P-bis(2-arylethyl)-P-(α-hydroxybenzyl) phosphine oxides, available from styrenes, phosphine and aldehydes. The cyclization proceeds in the presence of FeCl3 at 80°C, yield of the products is 53–60%.

References

1.
10.1016/j.mencom.2018.01.008_sbref0005a
Hewitt
1996
2.
10.1016/j.mencom.2018.01.008_sbref0005b
Gallagher
Phosphorus-Carbon Heterocyclic Chemistry, 2001
3.
10.1016/j.mencom.2018.01.008_sbref0005c
Edwards
2008
4.
A. W. Phelps and J. A. Sturgill, Patent WO 2004009869 A3, 2004.
5.
M. Miyagi, H. Yauchi and Y. Soneta, Patent JP 2009029857, 2009.
6.
D. G. T. Morimoto, K. Hiratsuka, Y. Sanada and H. Ariga, Patent JP 63305508, 1988.
7.
T. Hatakeyama, S. Hashimoto and M. Nakamura, Patent WO 2010104047 A1, 2010.
8.
Y. Qiu, H. Fan, J. Li and Y. Li, Patent CN 103183711, 2013.
9.
H. J. Lee,Y. J. Cho, H.J. Kwon, B.O. Kim, S.M. Kim and S. S. Yoon, EP 2145936 A3, 2010.
10.
Beletskaya I.P., Kabachnik M.M.
Mendeleev Communications, 2008
11.
Tatarinov D.A., Mironov V.F., Varaksina E.N., Krivolapov D.B., Litvinov I.A., Musin R.Z., Buzykin B.I., Konovalov A.I.
Mendeleev Communications, 2008
12.
Zagidullin A.A., Bezkishko I.A., Miluykov V.A., Sinyashin O.G.
Mendeleev Communications, 2013
13.
Dil’mukhametova L.K., Tyumkina T.V., D’yakonov V.A., Dzhemilev U.M.
Mendeleev Communications, 2017
14.
Nasibullin I.O., Nemtarev A.V., Mironov V.F.
Mendeleev Communications, 2017
15.
Knyazeva I.R., Matveeva V.I., Habicher W.D., Syakaev V.V., Gabidullin B.M., Gubaidullin A.T., Burilov A.R., Pudovik M.A.
Mendeleev Communications, 2017
16.
Sodium in liquid ammonia—a versatile tool in modifications of arylphosphine oxides
Stankevič M., Włodarczyk A., Jaklińska M., Parcheta R., Pietrusiewicz K.M.
Tetrahedron, 2011
17.
10.1016/j.mencom.2018.01.008_sbref0010b
Chen
Synthesis, 2014
21.
Reaction of Secondary Phosphine Oxides with Aromatic Aldehydes
Ivanova N.I., Reutskaya A.M., Gusarova N.K., Medvedeva S.A., Afonin A.V., Ushakov I.A., Tatarinova A.A., Trofimov B.A.
Russian Journal of General Chemistry, 2003
22.
Novel general halogen-free methodology for the synthesis of organophosphorus compounds
Gusarova N.K., Arbuzova S.N., Trofimov B.A.
Pure and Applied Chemistry, 2012
23.
Gusarova N.K., Malysheva S.F., Kuimov V.A., Belogorlova N.A., Mikhailenko V.L., Trofimov B.A.
Mendeleev Communications, 2008
24.
Catalyst- and Solvent-Free Rapid Addition of Secondary Phosphine Chalcogenides to Aldehydes: Another Click Chemistry
Gusarova N., Ivanova N., Volkov P., Khrapova K., Larina L., Smirnov V., Borodina T., Trofimov B.
Synthesis, 2015