Organic and Biomolecular Chemistry

, volume 14 , issue 4 , pages 1370-1381

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

Alexander S. Bogachenkov ¹

Albina V Dogadina ²

Irina A Boyarskaya ¹

Vadim P Boyarskiy ¹

Aleksander V Vasilyev ^{1, 3}

Hide authors affiliations Show authors affiliations: 3 affiliations

Department of Organic Chemistry, Institute of Chemistry, Saint Petersburg State University, Universitetskaya nab., 7/9, Saint Petersburg, Russia |

Department of Organic Chemistry, Saint Petersburg Institute of Technology (Technical University), Moskovskiy pr. 26, Saint Petersburg, Russia |

Department of Chemistry, Saint Petersburg State Forest Technical University, Institutsky per., 5, Saint Petersburg, Russia |

Publication type: Journal Article

Publication date: 2016-01-01

Royal Society of Chemistry (RSC)

Organic and Biomolecular Chemistry

scimago Q2

wos Q2

SJR: 0.600

CiteScore: 5.2

Impact factor: 2.7

ISSN: 14770520, 14770539

DOI: 10.1039/C5OB02143J

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PubMed ID: 26666315

Organic Chemistry

Biochemistry

Physical and Theoretical Chemistry

Abstract

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.

Found

1 citation

Vatsadze Sergey

DSc in Chemistry, professor, professor of the Russian Academy of Sciences

170 publications, 2 107 citations, 9 reviews

h-index: 20

N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

Research interests

Supramolecular chemistry

1 citation

Fedorov Alexey

DSc in Chemistry, associate member of the Russian Academy of Sciences

93 publications, 2 841 citations, 10 reviews

h-index: 27

Lobachevsky State University of Nizhny Novgorod

1 citation

Novikov Mikhail

DSc in Chemistry, associate professor

218 publications, 4 192 citations, 54 reviews

h-index: 33

Saint Petersburg State University

1 citation

Kinzhalov Mikhail

🥼 🤝

DSc in Chemistry, associate professor

97 publications, 1 919 citations

h-index: 28

National Research Tomsk Polytechnic University

Saint Petersburg State University

Research interests

Coordination Chemistry

Non-covalent Interactions

Organic Chemistry

Organometallic Chemistry

1 citation

Nyuchev Alexander

🥼 🤝

PhD in Chemistry

43 publications, 1 268 citations, 27 reviews

h-index: 19

Lobachevsky State University of Nizhny Novgorod

Research interests

Flow Chemistry

Flow-through microreactors

1 citation

Zubkov Fedor

🥼 🤝

DSc in Chemistry, professor

240 publications, 3 229 citations, 19 reviews

h-index: 31

Peoples' Friendship University of Russia

Research interests

Organic Chemistry

1 citation

Gazizov Almir

🥼

DSc in Chemistry

157 publications, 895 citations, 23 reviews

h-index: 14

A.E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center of the Russian Academy of Sciences

Research interests

Heterocyclic compounds

Organic Chemistry

Organophosphorus chemistry

1 citation

Chugunova Elena

🤝

DSc in Chemistry

62 publications, 532 citations, 1 review

h-index: 13

A.E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center of the Russian Academy of Sciences

Kazan National Research Technological University

1 citation

Aksenov Aleksandr

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DSc in Chemistry, professor

245 publications, 2 202 citations, 15 reviews

h-index: 24

North Caucasus Federal University

Research interests

Medicinal Chemistry

Organic Chemistry

1 citation

Zakharova Lucia

DSc in Chemistry, professor

394 publications, 6 176 citations

h-index: 37

A.E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center of the Russian Academy of Sciences

1 citation

Osyanin Vitaly

DSc in Chemistry, professor

131 publications, 1 144 citations, 3 reviews

h-index: 16

Samara State Technical University

Samara National Research University

Togliatti State University

Research interests

Organic Chemistry

1 citation

Tikhomirov Alexander

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DSc in Chemistry, associate professor

60 publications, 931 citations

h-index: 17

Mendeleev University of Chemical Technology of Russia

Gause Institute of New Antibiotics

Research interests

Medicinal Chemistry

1 citation

Abdelhamid Oussama

7 publications, 16 citations

h-index: 3

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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.

GOST all authors (up to 50) Copy

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.

RIS |

Cite this

RIS Copy

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 -

BibTex |

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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}

}

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.