Chemical Communications

, volume 54 , issue 23 , pages 2850-2853

Diels-Alder reactions between hexafluoro-2-butyne and bis-furyl dienes: kinetic versus thermodynamic control.

Kseniya K Borisova ^{1, 2, 3, 4, 5, 6}

Eugeniya V. Nikitina ^{1, 2, 3, 4, 5, 6}

Roman G. Novikov ^{5, 6, 7, 8, 9}

Victor N. Khrustalev ^{1, 2, 3, 4, 5, 6}

Pavel Dorovatovskii ^{5, 10, 11, 12}

Yan V. Zubavichus ^{5, 10, 11, 12}

Maxim Kuznetsov ^{13, 14, 15, 16, 17, 18}

Vladimir P. Zaytsev ^{1, 2, 3, 4, 5, 6}

Alexey V. Varlamov ^{1, 2, 3, 4, 5, 6}

Fedor I. Zubkov ^{1, 2, 3, 4, 5, 6}

Hide authors affiliations Show authors affiliations: 18 affiliations

Organic Chemistry Department, Faculty of Science, Peoples’ Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St., Moscow, Russian Federation |

Organic Chemistry Department

Faculty of science

⁴

Peoples’ Friendship University of Russia (RUDN University) |

⁵

Moscow

⁶

RUSSIAN FEDERATION |

⁷

V. A. Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, 32 Vavilov St., Moscow, Russian Federation |

⁸

V. A. Engelhardt Institute of Molecular Biology |

⁹

RUSSIAN ACADEMY OF SCIENCES

¹⁰

National Research Center “Kurchatov Institute”, 1 Acad. Kurchatov Sq., Moscow, Russia |

¹¹

National Research Center “Kurchatov Institute” |

¹²

Russia |

¹³

Centro de Química Estrutural, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais, Lisbon 1049-001, Portugal |

¹⁴

Centro de Química Estrutural

¹⁵

Instituto Superior Técnico |

¹⁶

Universidade de Lisboa |

¹⁷

Lisbon 1049-001 |

¹⁸

PORTUGAL |

Publication type: Journal Article

Publication date: 2018-02-02

Royal Society of Chemistry (RSC)

Chemical Communications

scimago Q1

wos Q2

SJR: 1.037

CiteScore: 7.4

Impact factor: 4.2

ISSN: 13597345, 1364548X

DOI: 10.1039/C7CC09466C

Copy DOI

PubMed ID: 29393318

Materials Chemistry

Metals and Alloys

Surfaces, Coatings and Films

General Chemistry

Ceramics and Composites

Electronic, Optical and Magnetic Materials

Catalysis

Abstract

The tandem [4+2] cycloaddition between hexafluoro-2-butyne and bis-furyl dienes, like difurfuryl ester, at room temperature leads to the kinetically controlled "pincer"-adducts - annulated 4a,8a-bis(trifluoromethyl)hexahydro-1,4:5,8-diepoxynaphthalenes. On the other hand, if these reactions proceed at 140 °C, only the thermodynamically controlled "domino"-adducts - annulated 2,3-bis(trifluoromethyl)hexahydro-1,4:5,8-diepoxynaphthalenes - are formed. Therefore, a very rare and unexpected example of full kinetic and thermodynamic control in the Diels-Alder reaction is reported in this paper.

Found

7 citations

Zubkov Fedor

🥼 🤝

DSc in Chemistry, professor

240 publications, 3 226 citations, 19 reviews

h-index: 31

Peoples' Friendship University of Russia

Research interests

Organic Chemistry

6 citations

Khrustalev Victor

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

324 publications, 4 032 citations, 4 reviews

h-index: 30

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

Peoples' Friendship University of Russia

5 citations

Kvyatkovskaya Elizaveta

14 publications, 91 citations

h-index: 6

Peoples' Friendship University of Russia

4 citations

Nikitina Evgeniya

PhD in Chemistry, associate professor

84 publications, 809 citations

h-index: 17

Peoples' Friendship University of Russia

3 citations

Dorovatovskii Pavel

340 publications, 3 990 citations

h-index: 28

National Research Centre "Kurchatov Institute"

1 citation

Novikov Alexander

🥼 🤝

PhD in Chemistry

412 publications, 8 117 citations, 251 reviews

h-index: 53

Saint Petersburg State University

Lomonosov Moscow State University

National Research University Higher School of Economics

Peoples' Friendship University of Russia

Research interests

Computational chemistry

Machine learning

Non-covalent Interactions

Quantum Chemistry

Reaction mechanisms

Supramolecular chemistry

1 citation

Bunev Alexander

🥼 🤝

83 publications, 461 citations, 291 reviews

h-index: 12

Togliatti State University

Research interests

Medicinal Chemistry

1 citation

Nelyubina Yulia

🤝

DSc in Chemistry

506 publications, 7 580 citations, 1 review

h-index: 38

A.N.Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences

Moscow Institute of Physics and Technology

Metal-organic frameworks

Quantum technologies

Sensors

1 citation

Kinzhalov Mikhail

🥼 🤝

DSc in Chemistry, associate professor

94 publications, 1 895 citations

h-index: 27

National Research Tomsk Polytechnic University

Saint Petersburg State University

Research interests

Coordination Chemistry

Non-covalent Interactions

Organic Chemistry

Organometallic Chemistry

1 citation

Baykov Sergey

🥼 🤝

PhD in Chemistry

99 publications, 1 345 citations, 15 reviews

h-index: 21

Saint Petersburg State University

1 citation

Antonova Alexandra

PhD in Chemistry

10 publications, 53 citations

h-index: 4

Peoples' Friendship University of Russia

A.N.Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences

Research interests

Coordination Chemistry

Organic Chemistry

1 citation

Sosnovskikh Vyacheslav

DSc in Chemistry, professor

355 publications, 4 721 citations

h-index: 30

Ural Federal University

1 citation

Pavlov Alexander

🥼 🤝

DSc in Chemistry

120 publications, 1 964 citations

h-index: 23

Bauman Moscow State Technical University

Kurnakov Institute of General and Inorganic Chemistry of the Russian Academy of Sciences

Mendeleev University of Chemical Technology of Russia

Research interests

Digital Chemistry

Digital Materials Science

Molecular magnetism

1 citation

Alekseeva Kseniia

16 publications, 100 citations

h-index: 5

Peoples' Friendship University of Russia

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GOST |

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GOST Copy

Borisova K. K. et al. Diels-Alder reactions between hexafluoro-2-butyne and bis-furyl dienes: kinetic versus thermodynamic control. // Chemical Communications. 2018. Vol. 54. No. 23. pp. 2850-2853.

GOST all authors (up to 50) Copy

Borisova K. K. et al. Diels-Alder reactions between hexafluoro-2-butyne and bis-furyl dienes: kinetic versus thermodynamic control. // Chemical Communications. 2018. Vol. 54. No. 23. pp. 2850-2853.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1039/C7CC09466C

UR - https://xlink.rsc.org/?DOI=C7CC09466C

TI - Diels-Alder reactions between hexafluoro-2-butyne and bis-furyl dienes: kinetic versus thermodynamic control.

T2 - Chemical Communications

AU - Borisova, Kseniya K

AU - Nikitina, Eugeniya V.

AU - Novikov, Roman G.

AU - Khrustalev, Victor N.

AU - Dorovatovskii, Pavel

AU - Zubavichus, Yan V.

AU - Kuznetsov, Maxim

AU - Zaytsev, Vladimir P.

AU - Varlamov, Alexey V.

AU - Zubkov, Fedor I.

PY - 2018

DA - 2018/02/02

PB - Royal Society of Chemistry (RSC)

SP - 2850-2853

IS - 23

VL - 54

PMID - 29393318

SN - 1359-7345

SN - 1364-548X

ER -

BibTex |

Cite this

BibTex (up to 50 authors) Copy

@article{2018_Borisova,

author = {Kseniya K Borisova and Eugeniya V. Nikitina and Roman G. Novikov and Victor N. Khrustalev and Pavel Dorovatovskii and Yan V. Zubavichus and Maxim Kuznetsov and Vladimir P. Zaytsev and Alexey V. Varlamov and Fedor I. Zubkov and others},

title = {Diels-Alder reactions between hexafluoro-2-butyne and bis-furyl dienes: kinetic versus thermodynamic control.},

journal = {Chemical Communications},

year = {2018},

volume = {54},

publisher = {Royal Society of Chemistry (RSC)},

month = {feb},

url = {https://xlink.rsc.org/?DOI=C7CC09466C},

number = {23},

pages = {2850--2853},

doi = {10.1039/C7CC09466C}

}

MLA

Cite this

MLA Copy

Borisova, Kseniya K., et al. “Diels-Alder reactions between hexafluoro-2-butyne and bis-furyl dienes: kinetic versus thermodynamic control..” Chemical Communications, vol. 54, no. 23, Feb. 2018, pp. 2850-2853. https://xlink.rsc.org/?DOI=C7CC09466C.

Publisher

Royal Society of Chemistry (RSC)

Journal

Chemical Communications

scimago Q1

wos Q2

SJR

1.037

CiteScore

7.4

Impact factor

4.2

ISSN

13597345 (Print)

1364548X (Electronic)

Labs

Laboratory of Organic Synthesis

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