Premium
Lewis Acid Catalyzed Reactions of Donor–Acceptor Cyclopropanes with Anthracenes
Author(s) -
Ivanova Olga A.,
Budynina Ekaterina M.,
Grishin Yuri K.,
Trushkov Igor V.,
Verteletskii Pavel V.
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200800620
Subject(s) - cyclopropane , chemistry , anthracene , aryl , intramolecular force , electrophile , friedel–crafts reaction , cycloaddition , lewis acids and bases , moiety , medicinal chemistry , ring (chemistry) , catalysis , photochemistry , stereochemistry , organic chemistry , alkyl
The reactions of 2‐aryl‐1,1‐cyclopropane diesters with anthracene derivatives were studied for the first time. Three kinds of reaction products are formed depending on the nature of the aryl group and the substituents in the anthracene. The first one is the product of [4+3] cycloaddition of cyclopropane to a diene moiety of anthracene. The second one also has a seven‐membered ring and is formed by the Lewis acid catalyzed electrophilic attack of cyclopropane onto the C9 atom of anthracene followed by intramolecular attack of the formed arenonium ion on aryl group of the starting cyclopropane. Lastly, the common Friedel–Crafts products are formed. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)