European Journal of Organic Chemistry

, volume 2019 , issue 26 , pages 4207-4214

Four-Membered Cycle Formation Challenge: GaCl3 -Promoted Formal [2+2]-Cycloaddition of Donor-Acceptor Cyclopropanes to Bicyclobutylidene

Maria A Zotova ^{1, 2}

Roman G. Novikov ^{1, 2, 3, 4}

Alexander D Volodin ⁵

Alexander Korlyukov ^{5, 6}

Alexander A. Korlyukov ^{7, 8}

Yaroslav V. Tkachev ³

Victor A Korolev ^{1, 2}

Yury V. Tomilov ^{1, 2}

Hide authors affiliations Show authors affiliations: 8 affiliations

N. D. Zelinsky Institute of Organic Chemistry; Russian Academy of Sciences; 47 Leninsky prosp. 119991 Moscow Russian Federation |

N. D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences 47 Leninsky prosp. 119991 Moscow Russian Federation |

Engelhardt Institute of Molecular Biology; Russian Academy of Sciences; 32 Vavilov st. 119991 Moscow Russian Federation |

⁴

Engelhardt Institute of Molecular Biology Russian Academy of Sciences 32 Vavilov st. 119991 Moscow Russian Federation |

⁵

Nesmeyanov Institute of Organoelement Compounds; Russian Academy of Sciences; Vavilov Str., 28 119991 Moscow Russia |

⁶

Pirogov Russian National Research Medical University; Ostrovitianov str. 1 117997 Moscow Russia |

⁷

Nesmeyanov Institute of Organoelement Compounds Russian Academy of Sciences Vavilov Str., 28 119991 Moscow Russia |

⁸

Pirogov Russian National Research Medical University Ostrovitianov Str. 1 117997 Moscow Russia |

Publication type: Journal Article

Publication date: 2019-05-16

Wiley

European Journal of Organic Chemistry

scimago Q2

wos Q2

SJR: 0.558

CiteScore: 4.3

Impact factor: 2.7

ISSN: 1434193X, 10990690

DOI: 10.1002/ejoc.201900329

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Organic Chemistry

Physical and Theoretical Chemistry

Abstract

The first selective process of formal [2+2]‐cycloaddition of donor–acceptor cyclopropanes (DAC) to multiple C–C bonds to form a four‐membered ring in the product has been developed. Bicyclobutylidene is used do demonstrate this reaction. The process is promoted by GaCl₃ and occurs through generation of 1,2‐zwitterionic intermediates. A carbocationic rearrangement occurs in the bicyclobutylidene moiety. It results in expansion of both cyclobutane rings into five‐membered ones and formation of a [2.3.3]propellane skeleton in the final product.

Found

2 citations

Potapov Konstantin

🥼

21 publications, 146 citations

h-index: 6

Engelhardt Institute of Molecular Biology of the Russian Academy of Sciences

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

1 citation

Uchuskin Maxim

🥼 🤝

PhD in Chemistry

56 publications, 778 citations

h-index: 16

Perm State National Research University

Research interests

Heterocyclic compounds

Organic synthesis

Synthetic Organic Chemistry

1 citation

Andreev Ivan

PhD in Chemistry

41 publications, 495 citations, 10 reviews

h-index: 12

Peoples' Friendship University of Russia

Dmitry Rogachev National Research Center of Pediatric Hematology, Oncology and Immunology

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

1 citation

Borisova Irina

🥼 🤝

PhD in Chemistry

7 publications, 46 citations

h-index: 5

Samara State Technical University

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

Research interests

Chemistry

Chemistry of heterocycles

Dyes (Dyes)

Organic and Medicinal Chemistry

1 citation

Ratova Daryya-mariya

3 publications, 21 citations

h-index: 3

Lomonosov Moscow State University

1 citation

Novikov Maxim

🥼 🤝

PhD in Chemistry

26 publications, 718 citations

h-index: 9

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

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Zotova M. A. et al. Four-Membered Cycle Formation Challenge: GaCl3 -Promoted Formal [2+2]-Cycloaddition of Donor-Acceptor Cyclopropanes to Bicyclobutylidene // European Journal of Organic Chemistry. 2019. Vol. 2019. No. 26. pp. 4207-4214.

GOST all authors (up to 50) Copy

Zotova M. A., Novikov R. G., Volodin A. D., Korlyukov A., Korlyukov A. A., Tkachev Y. V., Korolev V. A., Tomilov Y. V. Four-Membered Cycle Formation Challenge: GaCl3 -Promoted Formal [2+2]-Cycloaddition of Donor-Acceptor Cyclopropanes to Bicyclobutylidene // European Journal of Organic Chemistry. 2019. Vol. 2019. No. 26. pp. 4207-4214.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1002/ejoc.201900329

UR - https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.201900329

TI - Four-Membered Cycle Formation Challenge: GaCl3 -Promoted Formal [2+2]-Cycloaddition of Donor-Acceptor Cyclopropanes to Bicyclobutylidene

T2 - European Journal of Organic Chemistry

AU - Zotova, Maria A

AU - Novikov, Roman G.

AU - Volodin, Alexander D

AU - Korlyukov, Alexander

AU - Korlyukov, Alexander A.

AU - Tkachev, Yaroslav V.

AU - Korolev, Victor A

AU - Tomilov, Yury V.

PY - 2019

DA - 2019/05/16

PB - Wiley

SP - 4207-4214

IS - 26

VL - 2019

SN - 1434-193X

SN - 1099-0690

ER -

BibTex |

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BibTex (up to 50 authors) Copy

@article{2019_Zotova,

author = {Maria A Zotova and Roman G. Novikov and Alexander D Volodin and Alexander Korlyukov and Alexander A. Korlyukov and Yaroslav V. Tkachev and Victor A Korolev and Yury V. Tomilov},

title = {Four-Membered Cycle Formation Challenge: GaCl3 -Promoted Formal [2+2]-Cycloaddition of Donor-Acceptor Cyclopropanes to Bicyclobutylidene},

journal = {European Journal of Organic Chemistry},

year = {2019},

volume = {2019},

publisher = {Wiley},

month = {may},

url = {https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.201900329},

number = {26},

pages = {4207--4214},

doi = {10.1002/ejoc.201900329}

}

MLA

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MLA Copy

Zotova, Maria A., et al. “Four-Membered Cycle Formation Challenge: GaCl3 -Promoted Formal [2+2]-Cycloaddition of Donor-Acceptor Cyclopropanes to Bicyclobutylidene.” European Journal of Organic Chemistry, vol. 2019, no. 26, May. 2019, pp. 4207-4214. https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.201900329.