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Thiol elimination from tris[2-(phenylthio)ethyl]phosphine oxide: a convenient route to trivinylphosphine oxide

Nina Kuzminichna Gusarova 1
Nina Kuzminichna Gusarova
, 
Nataliya Alexeevna Chernysheva 1
Nataliya Alexeevna Chernysheva
, 
Svetlana Nikolaevna Arbuzova 1
Svetlana Nikolaevna Arbuzova
, 
Maria Vladimirovna Bogdanova 1
Maria Vladimirovna Bogdanova
, 
Nina Ivanovna Ivanova 1
Nina Ivanovna Ivanova
, 
Andrei Anatol'evich Kudryavtsev 1
Andrei Anatol'evich Kudryavtsev
, 
Boris Aleksandrovich Trofimov 1
Boris Aleksandrovich Trofimov
10.1070/MC2006v016n01ABEH002248
Published 2006-01-31
Communication , Volume 16, Issue 1, 31-31
6
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Gusarova N. K. et al. Thiol elimination from tris[2-(phenylthio)ethyl]phosphine oxide: a convenient route to trivinylphosphine oxide // Mendeleev Communications. 2006. Vol. 16. No. 1. pp. 31-31.
GOST all authors (up to 50) Copy
Gusarova N. K., Chernysheva N. A., Arbuzova S. N., Bogdanova M. V., Ivanova N. I., Kudryavtsev A. A., Trofimov B. A. Thiol elimination from tris[2-(phenylthio)ethyl]phosphine oxide: a convenient route to trivinylphosphine oxide // Mendeleev Communications. 2006. Vol. 16. No. 1. pp. 31-31.
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TY - JOUR
DO - 10.1070/MC2006v016n01ABEH002248
UR - https://mendcomm.colab.ws/publications/10.1070/MC2006v016n01ABEH002248
TI - Thiol elimination from tris[2-(phenylthio)ethyl]phosphine oxide: a convenient route to trivinylphosphine oxide
T2 - Mendeleev Communications
AU - Gusarova, Nina Kuzminichna
AU - Chernysheva, Nataliya Alexeevna
AU - Arbuzova, Svetlana Nikolaevna
AU - Bogdanova, Maria Vladimirovna
AU - Ivanova, Nina Ivanovna
AU - Kudryavtsev, Andrei Anatol'evich
AU - Trofimov, Boris Aleksandrovich
PY - 2006
DA - 2006/01/31
PB - Mendeleev Communications
SP - 31-31
IS - 1
VL - 16
ER -
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@article{2006_Gusarova,
author = {Nina Kuzminichna Gusarova and Nataliya Alexeevna Chernysheva and Svetlana Nikolaevna Arbuzova and Maria Vladimirovna Bogdanova and Nina Ivanovna Ivanova and Andrei Anatol'evich Kudryavtsev and Boris Aleksandrovich Trofimov},
title = {Thiol elimination from tris[2-(phenylthio)ethyl]phosphine oxide: a convenient route to trivinylphosphine oxide},
journal = {Mendeleev Communications},
year = {2006},
volume = {16},
publisher = {Mendeleev Communications},
month = {Jan},
url = {https://mendcomm.colab.ws/publications/10.1070/MC2006v016n01ABEH002248},
number = {1},
pages = {31--31},
doi = {10.1070/MC2006v016n01ABEH002248}
}
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Gusarova, Nina Kuzminichna, et al. “Thiol elimination from tris[2-(phenylthio)ethyl]phosphine oxide: a convenient route to trivinylphosphine oxide.” Mendeleev Communications, vol. 16, no. 1, Jan. 2006, pp. 31-31. https://mendcomm.colab.ws/publications/10.1070/MC2006v016n01ABEH002248.

Abstract

Tris[2-(phenylthio)ethyl]phosphine oxide reacts with sodium amide to afford trivinylphosphine oxide in a good yield. The reaction involves the generation of phosphoryl-stabilised carbanions, which further eliminate benzene thiolate anions.

References

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Vinyl Derivatives of the Metals. VI. Preparation, Properties and Some Reactions of Trivinyl Compounds of Group V Elements1,2
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Atom-Economic Synthesis of Tris[2-(organylthio)ethyl]phosphine Oxides from Phosphine and Vinyl Sulfides
Gusarova N.K., Ivanova N.I., Bogdanova M.V., Sinegovskaya L.M., Gusarov A.V., Trofimov B.A.
Phosphorus, Sulfur and Silicon and the Related Elements, 2005
5.
10.1070/MC2006v016n01ABEH002248_bib5
Trofimov
The Chemistry of Functional Groups. Supplement. The Chemistry of Sulfur-Containing Functional Groups, 1993