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A shortcut to tris[2-(4-hydroxyphenyl)ethyl]phosphine oxide and 2-(4-hydroxyphenyl)ethylphosphinic acid via reaction of elemental phosphorus with 4-tert-butoxystyrene

Alexandr Viktorovich Artem’ev 1
Alexandr Viktorovich Artem’ev
, 
Nina Kuzminichna Gusarova 1
Nina Kuzminichna Gusarova
, 
Anastasiya O Korocheva 1
Anastasiya O Korocheva
, 
Svetlana Filippovna Malysheva 1
Svetlana Filippovna Malysheva
, 
Yuriy Vasil'evich Gatilov 2
Yuriy Vasil'evich Gatilov
, 
Boris Aleksandrovich Trofimov 1
Boris Aleksandrovich Trofimov
10.1016/j.mencom.2013.12.009
Published 2013-12-12
Communication , Volume 24, Issue 1, 29-31
6
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Artem’ev A. V. et al. A shortcut to tris[2-(4-hydroxyphenyl)ethyl]phosphine oxide and 2-(4-hydroxyphenyl)ethylphosphinic acid via reaction of elemental phosphorus with 4-tert-butoxystyrene // Mendeleev Communications. 2013. Vol. 24. No. 1. pp. 29-31.
GOST all authors (up to 50) Copy
Artem’ev A. V., Gusarova N. K., Korocheva A. O., Malysheva S. F., Gatilov Y. V., Trofimov B. A. A shortcut to tris[2-(4-hydroxyphenyl)ethyl]phosphine oxide and 2-(4-hydroxyphenyl)ethylphosphinic acid via reaction of elemental phosphorus with 4-tert-butoxystyrene // Mendeleev Communications. 2013. Vol. 24. No. 1. pp. 29-31.
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TY - JOUR
DO - 10.1016/j.mencom.2013.12.009
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2013.12.009
TI - A shortcut to tris[2-(4-hydroxyphenyl)ethyl]phosphine oxide and 2-(4-hydroxyphenyl)ethylphosphinic acid via reaction of elemental phosphorus with 4-tert-butoxystyrene
T2 - Mendeleev Communications
AU - Artem’ev, Alexandr Viktorovich
AU - Gusarova, Nina Kuzminichna
AU - Korocheva, Anastasiya O
AU - Malysheva, Svetlana Filippovna
AU - Gatilov, Yuriy Vasil'evich
AU - Trofimov, Boris Aleksandrovich
PY - 2013
DA - 2013/12/12
PB - Mendeleev Communications
SP - 29-31
IS - 1
VL - 24
ER -
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@article{2013_Artem’ev,
author = {Alexandr Viktorovich Artem’ev and Nina Kuzminichna Gusarova and Anastasiya O Korocheva and Svetlana Filippovna Malysheva and Yuriy Vasil'evich Gatilov and Boris Aleksandrovich Trofimov},
title = {A shortcut to tris[2-(4-hydroxyphenyl)ethyl]phosphine oxide and 2-(4-hydroxyphenyl)ethylphosphinic acid via reaction of elemental phosphorus with 4-tert-butoxystyrene},
journal = {Mendeleev Communications},
year = {2013},
volume = {24},
publisher = {Mendeleev Communications},
month = {Dec},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2013.12.009},
number = {1},
pages = {29--31},
doi = {10.1016/j.mencom.2013.12.009}
}
MLA
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Artem’ev, Alexandr Viktorovich, et al. “A shortcut to tris[2-(4-hydroxyphenyl)ethyl]phosphine oxide and 2-(4-hydroxyphenyl)ethylphosphinic acid via reaction of elemental phosphorus with 4-tert-butoxystyrene.” Mendeleev Communications, vol. 24, no. 1, Dec. 2013, pp. 29-31. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2013.12.009.

Abstract

Red phosphorus reacts with 4-tert-butoxystyrene in KOH/DMSO system to afford (depending on the reaction conditions) tris(4-tert-but- oxyphenylethyl)phosphine oxide (48% yield) and/or 4-tert-butoxyphenylethylphosphinic acid (30% yield). The treatment of these products with aqueous HCl (45°C, 5min) quantitatively delivers tris[2-(4-hydroxyphenyl)ethyl]phosphine oxide and 2-(4-hydroxyphenyl)ethyl-phosphinic acid.

References

1.
The Chemistry of Organophosphorus Compounds, Vol. 2: Phosphine Oxides, Sulphides, Selenides and Tellurides, ed. F. R. Hartley, Wiley, NewYork, 1992.
2.
The Chemistry of Organophosphorus Compounds, Vol. 4: Ter- and Quinque-valent Phosphorus Acids and their Derivatives, ed. F. R. Hartley, Wiley, New York, 1996.
4.
10.1016/j.mencom.2013.12.009_sbref0010b
Sinou
Eur. J. Org. Chem., 2012
10.
M. Ito and H. Hirose, Japanese Patent 2000186186, 2000.(from Jpn. Kokai Tokkyo Koho).
11.
L. D. Timberlake, M.V. Hanson and E. B. Edwards, US Patent 20030148109 A1, 2003.
12.
J. Gan, B.A. King, N.H. Groot, L. Maecker, S.M. Tinetti and W. G. Stobby, Int. Patent WO 2003102060 A1, 2003.
13.
E. N. Peters and C. L. Braidwood, US Patent 20080171817 A1, 2008.
14.
E. N. Peters and C. L. Braidwood, Int. Patent WO 2008089314 A1, 2008.
15.
L. D. Timberlake, M.V. Hanson and J. D. Sibecker, US Patent 8404161 B2, 2013.
16.
Synthesis and Solid-State Structure of Substituted Arylphosphine Oxides
Whitaker C.M., Kott K.L., McMahon R.J.
Journal of Organic Chemistry, 1995
18.
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
19.
A short history of SHELX
Sheldrick G.M.
Acta Crystallographica Section A Foundations of Crystallography, 2007