Russian Chemical Bulletin, volume 62, issue 11, pages 2407-2423

Reaction of donor-acceptor cyclopropanes with 1,3-diphenylisobenzofuran. Lewis acid effect on the reaction pathway

A O Chagarovskiy ^{1, 2}

O. A. Ivanova ¹

E M Budynina ^{1, 2}

E L Kolychev ¹

M S Nechaev ¹

I V Trushkov ^{1, 2}

M Ya Melnikov ¹

Hide authors affiliations Show authors affiliations: 2 affiliations

Department of Chemistry, M. V. Lomonosov Moscow State University, Moscow, Russian Federation |

D. Rogachev Federal Research Center of Pediatric Hematology, Oncology, and Immunology, Moscow, Russian Federation |

Publication type: Journal Article

Publication date: 2013-11-01

Springer Nature

Journal: Russian Chemical Bulletin

SJR: 0.292

CiteScore: 2.7

Impact factor: 1.7

ISSN: 10665285, 15739171

DOI: 10.1007/s11172-013-0349-x

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General Chemistry

Abstract

Reaction of donor-acceptor cyclopropanes with 1,3-diphenylisobenzofuran in the presence of lanthanide triflates, as well as CuOTf, Sn(OTf)2, SnCl2, ZnCl2, GaCl3, and MgI2, proceeds as a formal [3+4]-cycloaddition leading to a newly formed seven-membered ring. This reaction was found to be typical of cyclopropane-1,1-diesters and dinitriles, as well as 1-nitrocyclo-propanecarboxylates containing aromatic, heteroaromatic, and vinylic substituents at the C(2) atom of the small ring. When Me3SiOTf, TiCl4, SnCl4, or BF3·OEt2 were used as initiators, unusual cyclic hemiacetals were formed via the conjugate 1,4-addition of a cyclopropane and a nucleophile to the diene moiety.

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Chagarovskiy A. O. et al. Reaction of donor-acceptor cyclopropanes with 1,3-diphenylisobenzofuran. Lewis acid effect on the reaction pathway // Russian Chemical Bulletin. 2013. Vol. 62. No. 11. pp. 2407-2423.

GOST all authors (up to 50) Copy

Chagarovskiy A. O., Ivanova O. A., Budynina E. M., Kolychev E. L., Nechaev M. S., Trushkov I. V., Melnikov M. Ya. Reaction of donor-acceptor cyclopropanes with 1,3-diphenylisobenzofuran. Lewis acid effect on the reaction pathway // Russian Chemical Bulletin. 2013. Vol. 62. No. 11. pp. 2407-2423.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1007/s11172-013-0349-x

UR - https://doi.org/10.1007/s11172-013-0349-x

TI - Reaction of donor-acceptor cyclopropanes with 1,3-diphenylisobenzofuran. Lewis acid effect on the reaction pathway

T2 - Russian Chemical Bulletin

AU - Chagarovskiy, A O

AU - Ivanova, O. A.

AU - Budynina, E M

AU - Kolychev, E L

AU - Nechaev, M S

AU - Trushkov, I V

AU - Melnikov, M Ya

PY - 2013

DA - 2013/11/01

PB - Springer Nature

SP - 2407-2423

IS - 11

VL - 62

SN - 1066-5285

SN - 1573-9171

ER -

BibTex |

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BibTex (up to 50 authors) Copy

@article{2013_Chagarovskiy,

author = {A O Chagarovskiy and O. A. Ivanova and E M Budynina and E L Kolychev and M S Nechaev and I V Trushkov and M Ya Melnikov},

title = {Reaction of donor-acceptor cyclopropanes with 1,3-diphenylisobenzofuran. Lewis acid effect on the reaction pathway},

journal = {Russian Chemical Bulletin},

year = {2013},

volume = {62},

publisher = {Springer Nature},

month = {nov},

url = {https://doi.org/10.1007/s11172-013-0349-x},

number = {11},

pages = {2407--2423},

doi = {10.1007/s11172-013-0349-x}

}

MLA

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MLA Copy

Chagarovskiy, A. O., et al. “Reaction of donor-acceptor cyclopropanes with 1,3-diphenylisobenzofuran. Lewis acid effect on the reaction pathway.” Russian Chemical Bulletin, vol. 62, no. 11, Nov. 2013, pp. 2407-2423. https://doi.org/10.1007/s11172-013-0349-x.

Found error?

Publisher

Springer Nature

Journal

Russian Chemical Bulletin

SJR

0.292

CiteScore

2.7

Impact factor

1.7

ISSN

10665285 (Print)

15739171 (Electronic)