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

Журнал European Journal of Organic Chemistry
ISSN: 1434-193X , E-ISSN: 1099-0690
Вых. Данные Год: 2019, Том: 2019, Номер: 26, Страницы: 4207-4214 Страниц : 8 DOI: 10.1002/ejoc.201900329
Авторы Zotova Maria A. 1 , Novikov Roman A. 2,1 , Volodin Alexander D. 3 , Korlyukov Alexander A. 3,4 , Tkachev Yaroslav V. 2 , Korolev Victor A. 1 , Tomilov Yury V. 1
Организации
1 N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation
2 Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, 32 Vavilov st., 119991 Moscow, Russian Federation
3 Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov Str., 28, 119991 Moscow, Russia
4 Pirogov Russian National Research Medical University, Ostrovitianov str. 1, 117997 Moscow, Russia

Реферат: 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.
Библиографическая ссылка: Zotova M.A. , Novikov R.A. , Volodin A.D. , 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. V.2019. N26. P.4207-4214. DOI: 10.1002/ejoc.201900329 WOS Scopus OpenAlex
Идентификаторы БД:
≡ Web of science: WOS:000475679400014
≡ Scopus: 2-s2.0-85066051092
≡ OpenAlex: W2938867992
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