Synthesis of 1,4-dihydrophosphinoline 1-oxides by acid-promoted cyclization of 1-(diphenylphosphoryl)allenes

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Synthesis of 1,4-dihydrophosphinoline 1-oxides by acid-promoted cyclization of 1-(diphenylphosphoryl)allenes. / Bogachenkov, Alexander S.; Dogadina, Albina V.; Boyarskaya, Irina A.; Boyarskiy, Vadim P.; Vasilyev, Aleksander V.

в: Organic and Biomolecular Chemistry, Том 14, № 4, 2016, стр. 1370-1381.

Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование

BibTeX

@article{0269230ded314c78870d25632956e4f1,

title = "Synthesis of 1,4-dihydrophosphinoline 1-oxides by acid-promoted cyclization of 1-(diphenylphosphoryl)allenes",

abstract = "1-(Diphenylphosphoryl)alka-1,2-dienes (phosphonoallenes) in Br{\o}nsted (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.",

author = "Bogachenkov, {Alexander S.} and Dogadina, {Albina V.} and Boyarskaya, {Irina A.} and Boyarskiy, {Vadim P.} and Vasilyev, {Aleksander V.}",

note = "Funding Information: This work was supported by Saint Petersburg State University (grant no. 12.50.2525.2013 and no. 12.38.195.2014). Spectral studies were performed at the Center for Magnetic Resonance, the Center for Chemical Analysis and Materials Research, and the Research Center for X-ray Diffraction Studies of Saint Petersburg State University. Publisher Copyright: {\textcopyright} The Royal Society of Chemistry 2016. Copyright: Copyright 2016 Elsevier B.V., All rights reserved.",

year = "2016",

doi = "10.1039/c5ob02143j",

language = "English",

volume = "14",

pages = "1370--1381",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "4",

}

RIS

TY - JOUR

T1 - Synthesis of 1,4-dihydrophosphinoline 1-oxides by acid-promoted cyclization of 1-(diphenylphosphoryl)allenes

AU - Bogachenkov, Alexander S.

AU - Dogadina, Albina V.

AU - Boyarskaya, Irina A.

AU - Boyarskiy, Vadim P.

AU - Vasilyev, Aleksander V.

N1 - Funding Information: This work was supported by Saint Petersburg State University (grant no. 12.50.2525.2013 and no. 12.38.195.2014). Spectral studies were performed at the Center for Magnetic Resonance, the Center for Chemical Analysis and Materials Research, and the Research Center for X-ray Diffraction Studies of Saint Petersburg State University. Publisher Copyright: © The Royal Society of Chemistry 2016. Copyright: Copyright 2016 Elsevier B.V., All rights reserved.

PY - 2016

Y1 - 2016

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=84955471184&partnerID=8YFLogxK

U2 - 10.1039/c5ob02143j

DO - 10.1039/c5ob02143j

M3 - Article

VL - 14

SP - 1370

EP - 1381

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

SN - 1477-0520

IS - 4

ER -

ID: 7549342