Nucleophilic addition of secondary phosphine chalcogenides to, α,β-acetylenic γ-hydroxy acid nitriles and a rearrangement of the adducts
Svetlana N Arbuzova
1, 2, 3, 4, 5
,
Nina K. Gusarova
1, 2, 3, 4, 5
,
Maria V. Bogdanova
1, 2, 3, 4, 5
,
Igor Ushakov
1, 2, 3, 4, 5
,
Anastasiya G. Mal’kina
1, 2, 3, 4, 5
,
B. A. Trofimov
1, 2, 3, 4, 5
2
Siberian branch of the Russian Academy of sciences
3
664033
4
Irkutsk
|
5
RUSSIAN FEDERATION
|
Publication type: Journal Article
Publication date: 2007-11-01
scimago Q3
wos Q3
SJR: 0.305
CiteScore: 3.0
Impact factor: 1.7
ISSN: 09599436, 1364551X
General Chemistry
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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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.
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Arbuzova S. N., Gusarova N. K., Bogdanova M. V., Ushakov I., 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://doi.org/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 N
AU - Gusarova, Nina K.
AU - Bogdanova, Maria V.
AU - Ushakov, Igor
AU - Mal’kina, Anastasiya G.
AU - Trofimov, B. A.
PY - 2007
DA - 2007/11/01
PB - OOO Zhurnal "Mendeleevskie Soobshcheniya"
SP - 325-326
IS - 6
VL - 17
SN - 0959-9436
SN - 1364-551X
ER -
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BibTex (up to 50 authors)
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@article{2007_Arbuzova,
author = {Svetlana N Arbuzova and Nina K. Gusarova and Maria V. Bogdanova and Igor Ushakov and Anastasiya G. Mal’kina and B. A. 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 = {OOO Zhurnal "Mendeleevskie Soobshcheniya"},
month = {nov},
url = {https://doi.org/10.1016/j.mencom.2007.11.008},
number = {6},
pages = {325--326},
doi = {10.1016/j.mencom.2007.11.008}
}
Cite this
MLA
Copy
Arbuzova, Svetlana 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, vol. 17, no. 6, Nov. 2007, pp. 325-326. https://doi.org/10.1016/j.mencom.2007.11.008.