Synthesis of 1,4-dihydrophosphinoline 1-oxides by acid-promoted cyclization of 1-(diphenylphosphoryl)allenes
Тип публикации: Journal Article
Дата публикации: 2016-01-01
scimago Q2
wos Q2
БС1
SJR: 0.600
CiteScore: 5.2
Impact factor: 2.7
ISSN: 14770520, 14770539
PubMed ID:
26666315
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Краткое описание
1-(Diphenylphosphoryl)alka-1,2-dienes (phosphonoallenes) in Brønsted (super)acids (TfOH, FSO3H, H2SO4) gave the corresponding 1,2-oxaphosphol-3-enium ions, that were studied by means of NMR and DFT calculations. Upon hydrolysis of reaction solution, these cations afforded 3-hydroxyalk-2-en-1-yl-diphenylphosphine oxides (phosphonoallyl alcohols). But in (super)acids the cations were slowly transformed into O-protonated forms of 1-phenyl-1,4-dihydrophosphinoline 1-oxides, which were monitored by NMR. The latter phosphaheterocycles can be directly obtained from phosphonoallenes under the action of Lewis acid AlCl3.
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Bogachenkov A. S. et al. Synthesis of 1,4-dihydrophosphinoline 1-oxides by acid-promoted cyclization of 1-(diphenylphosphoryl)allenes // Organic and Biomolecular Chemistry. 2016. Vol. 14. No. 4. pp. 1370-1381.
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Bogachenkov A. S., Dogadina A. V., Boyarskaya I. A., Boyarskiy V. P., Vasilyev A. V. Synthesis of 1,4-dihydrophosphinoline 1-oxides by acid-promoted cyclization of 1-(diphenylphosphoryl)allenes // Organic and Biomolecular Chemistry. 2016. Vol. 14. No. 4. pp. 1370-1381.
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TY - JOUR
DO - 10.1039/C5OB02143J
UR - https://doi.org/10.1039/C5OB02143J
TI - Synthesis of 1,4-dihydrophosphinoline 1-oxides by acid-promoted cyclization of 1-(diphenylphosphoryl)allenes
T2 - Organic and Biomolecular Chemistry
AU - Bogachenkov, Alexander S.
AU - Dogadina, Albina V
AU - Boyarskaya, Irina A
AU - Boyarskiy, Vadim P
AU - Vasilyev, Aleksander V
PY - 2016
DA - 2016/01/01
PB - Royal Society of Chemistry (RSC)
SP - 1370-1381
IS - 4
VL - 14
PMID - 26666315
SN - 1477-0520
SN - 1477-0539
ER -
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@article{2016_Bogachenkov,
author = {Alexander S. Bogachenkov and Albina V Dogadina and Irina A Boyarskaya and Vadim P Boyarskiy and Aleksander V Vasilyev},
title = {Synthesis of 1,4-dihydrophosphinoline 1-oxides by acid-promoted cyclization of 1-(diphenylphosphoryl)allenes},
journal = {Organic and Biomolecular Chemistry},
year = {2016},
volume = {14},
publisher = {Royal Society of Chemistry (RSC)},
month = {jan},
url = {https://doi.org/10.1039/C5OB02143J},
number = {4},
pages = {1370--1381},
doi = {10.1039/C5OB02143J}
}
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MLA
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Bogachenkov, Alexander S., et al. “Synthesis of 1,4-dihydrophosphinoline 1-oxides by acid-promoted cyclization of 1-(diphenylphosphoryl)allenes.” Organic and Biomolecular Chemistry, vol. 14, no. 4, Jan. 2016, pp. 1370-1381. https://doi.org/10.1039/C5OB02143J.