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

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

Journal

European Journal of Organic Chemistry
ISSN: 1434-193X , E-ISSN: 1099-0690

Output data

Year: 2019, Volume: 2019, Number: 26, Pages: 4207-4214 Pages count : 8 DOI: 10.1002/ejoc.201900329

Authors

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

Affiliations

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

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.

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

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