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Nucleophilic addition of secondary phosphine chalcogenides to, α,β-acetylenic γ-hydroxy acid nitriles and a rearrangement of the adducts

Svetlana Nikolaevna Arbuzova 1
Svetlana Nikolaevna Arbuzova
, 
Nina Kuzminichna Gusarova 1
Nina Kuzminichna Gusarova
, 
Maria Vladimirovna Bogdanova 1
Maria Vladimirovna Bogdanova
, 
Igor Alekseevich Ushakov 1
Igor Alekseevich Ushakov
, 
Anastasiya Grigor'evna Mal'kina 1
Anastasiya Grigor'evna Mal'kina
, 
Boris Aleksandrovich Trofimov 1
Boris Aleksandrovich Trofimov
10.1016/j.mencom.2007.11.008
Published 2007-11-09
Communication , Volume 17, Issue 6, 325-326
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Arbuzova S. N. et al. Nucleophilic addition of secondary phosphine chalcogenides to, α,β-acetylenic γ-hydroxy acid nitriles and a rearrangement of the adducts // Mendeleev Communications. 2007. Vol. 17. No. 6. pp. 325-326.
GOST all authors (up to 50) Copy
Arbuzova S. N., Gusarova N. K., Bogdanova M. V., Ushakov I. A., Mal'kina A. G., Trofimov B. A. Nucleophilic addition of secondary phosphine chalcogenides to, α,β-acetylenic γ-hydroxy acid nitriles and a rearrangement of the adducts // Mendeleev Communications. 2007. Vol. 17. No. 6. pp. 325-326.
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TY - JOUR
DO - 10.1016/j.mencom.2007.11.008
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2007.11.008
TI - Nucleophilic addition of secondary phosphine chalcogenides to, α,β-acetylenic γ-hydroxy acid nitriles and a rearrangement of the adducts
T2 - Mendeleev Communications
AU - Arbuzova, Svetlana Nikolaevna
AU - Gusarova, Nina Kuzminichna
AU - Bogdanova, Maria Vladimirovna
AU - Ushakov, Igor Alekseevich
AU - Mal'kina, Anastasiya Grigor'evna
AU - Trofimov, Boris Aleksandrovich
PY - 2007
DA - 2007/11/09
PB - Mendeleev Communications
SP - 325-326
IS - 6
VL - 17
ER -
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@article{2007_Arbuzova,
author = {Svetlana Nikolaevna Arbuzova and Nina Kuzminichna Gusarova and Maria Vladimirovna Bogdanova and Igor Alekseevich Ushakov and Anastasiya Grigor'evna Mal'kina and Boris Aleksandrovich Trofimov},
title = {Nucleophilic addition of secondary phosphine chalcogenides to, α,β-acetylenic γ-hydroxy acid nitriles and a rearrangement of the adducts},
journal = {Mendeleev Communications},
year = {2007},
volume = {17},
publisher = {Mendeleev Communications},
month = {Nov},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2007.11.008},
number = {6},
pages = {325--326},
doi = {10.1016/j.mencom.2007.11.008}
}
MLA
Cite this
MLA Copy
Arbuzova, Svetlana Nikolaevna, et al. “Nucleophilic addition of secondary phosphine chalcogenides to, α,β-acetylenic γ-hydroxy acid nitriles and a rearrangement of the adducts.” Mendeleev Communications, vol. 17, no. 6, Nov. 2007, pp. 325-326. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2007.11.008.

Abstract

Bis(2-phenylethyl)phosphine oxide and sulfide and bis[2-(2-pyridyl)ethyl]phosphine sulfide add easily (LiOH–THF, 28–30°C) to 4-hydroxy-4-methyl-2-pentynenitrile to give regio- and stereoselectively 3-substituted (Z)-4-hydroxy-4-methyl-2-pentenenitriles in 82–91% yield; the latter, upon heating (58–60°C) in the presence of LiOH in THF, rearrange cleanly to the corresponding 3-cyano-2-propen-1-yl phosphinates and phosphinothioates (isolated yields of 82–86%).

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