Competition of (3+2) annulation and (3+2) cycloaddition in the reaction of alkenes with donor-acceptor cyclopropanes

Competition of (3+2) annulation and (3+2) cycloaddition in the reaction of alkenes with donor-acceptor cyclopropanes Full article

Journal

Russian Chemical Bulletin
ISSN: 1573-9171 , E-ISSN: 1066-5285

Output data

Year: 2024, Volume: 73, Number: 5, Pages: 1237-1252 Pages count : 16 DOI: 10.1007/s11172-024-4240-8

Authors

Volkova Yu.A. ¹ , Boichenko M.A. ² , Shorokhov V.V. ² , Zhokhov S.S. ² , Andreev I.A. ³ , Ratmanova N.K. ³ , Trushkov I.V. ¹ , Ivanova O.A. ²

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation
2	Department of Chemistry, Lomonosov Moscow State University, Build. 3, 1 Leninskie Gory, 119991, Moscow, Russian Federation
3	Dmitry Rogachev National Medical Research Center of Pediatric Hematology, Oncology and Immunology, 1 ul. Samory Mashela, 117997, Moscow, Russian Federation

Lewis acid-initiated reaction of (het)aryl-substituted donor-acceptor cyclopropanes with styrenes was studied. The initiation of the process by tin(IV) chloride caused the reaction to proceed in two alternative directions, namely, with the formation of substituted cyclopentanes ((3+2) cycloaddition products) and substituted indanes or their hetero analogs ((3+2) annulation products). The chemoselectivity of the reaction was controlled by several factors, such as the reaction conditions and the nature of reacting compounds and initiator.

Volkova Y.A. , Boichenko M.A. , Shorokhov V.V. , Zhokhov S.S. , Andreev I.A. , Ratmanova N.K. , Trushkov I.V. , Ivanova O.A.
Competition of (3+2) annulation and (3+2) cycloaddition in the reaction of alkenes with donor-acceptor cyclopropanes
Russian Chemical Bulletin. 2024. V.73. N5. P.1237-1252. DOI: 10.1007/s11172-024-4240-8 WOS Scopus OpenAlex

Web of science:	WOS:001252371600037
Scopus:	2-s2.0-85196641916
OpenAlex:	W4399897750

DB	Citing
OpenAlex	2
Scopus	2
Web of science	2