, volume 70 , issue 43 , pages 7865-7873

Multi-channel transformations of 1,3-diarylpropynones under superelectrophilic activation conditions: concurrence of intra- and intermolecular reactions. Experimental and theoretical study

Dmitry S. Ryabukhin ¹

Georgy K. Fukin ²

Aleksander V Vasilyev ³

Hide authors affiliations Show authors affiliations: 3 affiliations

Department of Organic Chemistry, Faculty of Chemistry, Saint Petersburg State University, Universitetsky pr. 26, Petrodvoretz, Saint-Petersburg 198504, Russia |

Institute of Organometallic Chemistry of Russian Academy of Science, Tropinina st., 49, Nizhny Novgorod 603950, Russia |

Department of Organic Chemistry, Faculty of Chemistry, Saint Petersburg State University, Universitetsky pr., 26, Petrodvoretz, Saint-Petersburg 198504, Russia |

Publication type: Journal Article

Publication date: 2014-10-01

Elsevier

Tetrahedron

scimago Q3

wos Q2

SJR: 0.426

CiteScore: 4.1

Impact factor: 2.2

ISSN: 00404020, 14645416

DOI: 10.1016/j.tet.2014.09.006

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Organic Chemistry

Drug Discovery

Biochemistry

Abstract

1,3-Diarypropynones undergo concurrent multi-channel transformations in Bronsted (FSO3H, TfOH) and Bronsted–Lewis (HF–SbF5, TfOH-SbF5) superacids, leading intramolecularly to 3-arylindenones, or intermolecularly to 1,3,3-triarylpropenones, and dimeric structures. The outcome depends on the electronic donor-acceptor properties of the substituents in the aromatic rings of the 1,3-diarylpropynones, and on the added aromatic external π-nucleophiles. The orbital energies, atom charges, orbital contributions, and global electrophilicity indices of the cationic intermediates have been calculated by DFT methods to explain these transformations.

Found

2 citations

Ryabukhin Dmitry

PhD in Chemistry

56 publications, 840 citations

h-index: 13

Saint-Petersburg State Forest Technical University

V. M. Gorbatov Federal Research Center for Food Systems of Russian Academy of Sciences

1 citation

Vatsadze Sergey

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

169 publications, 2 094 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, 2 810 citations, 10 reviews

h-index: 27

Lobachevsky State University of Nizhny Novgorod

1 citation

Novikov Mikhail

DSc in Chemistry, associate professor

215 publications, 4 151 citations, 54 reviews

h-index: 33

Saint Petersburg State University

1 citation

Nyuchev Alexander

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PhD in Chemistry

43 publications, 1 258 citations, 27 reviews

h-index: 19

Lobachevsky State University of Nizhny Novgorod

Research interests

Flow Chemistry

Flow-through microreactors

1 citation

Zubkov Fedor

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DSc in Chemistry, professor

240 publications, 3 223 citations, 19 reviews

h-index: 31

Peoples' Friendship University of Russia

Research interests

Organic Chemistry

1 citation

Aksenov Aleksandr

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DSc in Chemistry, professor

243 publications, 2 163 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, 6 131 citations

h-index: 36

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, 1 133 citations, 3 reviews

h-index: 16

Samara State Technical University

Research interests

Organic Chemistry

1 citation

Tikhomirov Alexander

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DSc in Chemistry, associate professor

59 publications, 910 citations

h-index: 17

Mendeleev University of Chemical Technology of Russia

Gause Institute of New Antibiotics

Research interests

Medicinal Chemistry

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Ryabukhin D. S., Fukin G. K., Vasilyev A. V. Multi-channel transformations of 1,3-diarylpropynones under superelectrophilic activation conditions: concurrence of intra- and intermolecular reactions. Experimental and theoretical study // Tetrahedron. 2014. Vol. 70. No. 43. pp. 7865-7873.

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RIS Copy

TY - JOUR

DO - 10.1016/j.tet.2014.09.006

UR - https://doi.org/10.1016/j.tet.2014.09.006

TI - Multi-channel transformations of 1,3-diarylpropynones under superelectrophilic activation conditions: concurrence of intra- and intermolecular reactions. Experimental and theoretical study

T2 - Tetrahedron

AU - Ryabukhin, Dmitry S.

AU - Fukin, Georgy K.

AU - Vasilyev, Aleksander V

PY - 2014

DA - 2014/10/01

PB - Elsevier

SP - 7865-7873

IS - 43

VL - 70

SN - 0040-4020

SN - 1464-5416

ER -

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@article{2014_Ryabukhin,

author = {Dmitry S. Ryabukhin and Georgy K. Fukin and Aleksander V Vasilyev},

title = {Multi-channel transformations of 1,3-diarylpropynones under superelectrophilic activation conditions: concurrence of intra- and intermolecular reactions. Experimental and theoretical study},

journal = {Tetrahedron},

year = {2014},

volume = {70},

publisher = {Elsevier},

month = {oct},

url = {https://doi.org/10.1016/j.tet.2014.09.006},

number = {43},

pages = {7865--7873},

doi = {10.1016/j.tet.2014.09.006}

}

MLA

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MLA Copy

Ryabukhin, Dmitry S., et al. “Multi-channel transformations of 1,3-diarylpropynones under superelectrophilic activation conditions: concurrence of intra- and intermolecular reactions. Experimental and theoretical study.” Tetrahedron, vol. 70, no. 43, Oct. 2014, pp. 7865-7873. https://doi.org/10.1016/j.tet.2014.09.006.

Publisher

Elsevier

Journal

Tetrahedron

scimago Q3

wos Q2

SJR

0.426

CiteScore

4.1

Impact factor

2.2

ISSN

00404020 (Print)

14645416 (Electronic)

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