Journal of Organic Chemistry

, том 84 , издание 7 , страницы 4534-4542

Rh(II)-Catalyzed Spirocyclization of α-Diazo Homophthalimides with Cyclic Ethers.

Тип публикации: Journal Article

Дата публикации: 2019-02-28

American Chemical Society (ACS)

Journal of Organic Chemistry

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SJR: 0.737

CiteScore: 6.1

Impact factor: 3.6

ISSN: 00223263, 15206904

DOI: 10.1021/acs.joc.9b00245

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PubMed ID: 30816715

Organic Chemistry

Краткое описание

Rh(II)-catalyzed decomposition of α-diazo homophthalimides in the presence of cyclic ethers gave spirocyclic products of Stevens-type [1,2]-alkyl shift within the postulated oxonium ylide intermediate. Such a reaction pathway is in line with thermodynamic predictions obtained from quantum chemical calculations performed at the B3LYP/6-31G* and B3LYP/6-311++G** levels of theory. These findings represent the first systematically investigated case of spirocyclization of cyclic α-diazocarbonyl compounds with cyclic ethers.

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Guranova N. I. et al. Rh(II)-Catalyzed Spirocyclization of α-Diazo Homophthalimides with Cyclic Ethers. // Journal of Organic Chemistry. 2019. Vol. 84. No. 7. pp. 4534-4542.

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Guranova N. I., Darin D., Kantin G., Novikov A. S., Bakulina O., Krasavin M. Rh(II)-Catalyzed Spirocyclization of α-Diazo Homophthalimides with Cyclic Ethers. // Journal of Organic Chemistry. 2019. Vol. 84. No. 7. pp. 4534-4542.

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TY - JOUR

DO - 10.1021/acs.joc.9b00245

UR - https://doi.org/10.1021/acs.joc.9b00245

TI - Rh(II)-Catalyzed Spirocyclization of α-Diazo Homophthalimides with Cyclic Ethers.

T2 - Journal of Organic Chemistry

AU - Guranova, Natalia I

AU - Darin, Dmitry

AU - Kantin, Grigory

AU - Novikov, Alexander S.

AU - Bakulina, Olga

AU - Krasavin, Mikhail

PY - 2019

DA - 2019/02/28

PB - American Chemical Society (ACS)

SP - 4534-4542

IS - 7

VL - 84

PMID - 30816715

SN - 0022-3263

SN - 1520-6904

ER -

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@article{2019_Guranova,

author = {Natalia I Guranova and Dmitry Darin and Grigory Kantin and Alexander S. Novikov and Olga Bakulina and Mikhail Krasavin},

title = {Rh(II)-Catalyzed Spirocyclization of α-Diazo Homophthalimides with Cyclic Ethers.},

journal = {Journal of Organic Chemistry},

year = {2019},

volume = {84},

publisher = {American Chemical Society (ACS)},

month = {feb},

url = {https://doi.org/10.1021/acs.joc.9b00245},

number = {7},

pages = {4534--4542},

doi = {10.1021/acs.joc.9b00245}

}

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Guranova, Natalia I., et al. “Rh(II)-Catalyzed Spirocyclization of α-Diazo Homophthalimides with Cyclic Ethers..” Journal of Organic Chemistry, vol. 84, no. 7, Feb. 2019, pp. 4534-4542. https://doi.org/10.1021/acs.joc.9b00245.