A New Type of Donor-Acceptor Cyclopropane Reactivity: The Generation of Formal 1,2- and 1,4-Dipoles

A new type of donor–acceptor cyclopropane reactivity has been discovered. On treatment with anhydrous GaCl3, they react as sources of even‐numbered 1,2‐ and 1,4‐dipoles instead of the classical odd‐numbered 1,3‐dipoles due to migration of positive charge from the benzyl center. This type of reactivi...

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Published in:	Angewandte Chemie International Edition Vol. 53; no. 12; pp. 3187 - 3191
Main Authors:	Novikov, Roman A., Tarasova, Anna V., Korolev, Victor A., Timofeev, Vladimir P., Tomilov, Yury V.
Format:	Journal Article
Language:	English
Published:	Weinheim WILEY-VCH Verlag 17-03-2014 WILEY‐VCH Verlag Wiley Subscription Services, Inc
Edition:	International ed. in English
Subjects:	annulation carbocycles Charge cyclodimerization Cyclopropane donor-acceptor systems Formations lewis acids Migration Strategy carbocycles donor-acceptor systems cyclodimerization annulation lewis acids
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Abstract	A new type of donor–acceptor cyclopropane reactivity has been discovered. On treatment with anhydrous GaCl3, they react as sources of even‐numbered 1,2‐ and 1,4‐dipoles instead of the classical odd‐numbered 1,3‐dipoles due to migration of positive charge from the benzyl center. This type of reactivity has been demonstrated for new reactions, namely, cyclodimerizations of donor–acceptor cyclopropanes that occur as [2+2]‐, [3+2]‐, [4+2]‐, [5+2]‐, [4+3]‐, and [5+4]‐annulations. The [4+2]‐annulation of 2‐arylcyclopropane‐1,1‐dicarboxylates to give polysubstituted 2‐aryltetralins has been developed in a preparative version that provides exceedingly high regio‐ and diastereoselectivity and high yields. The strategy for selective hetero‐combination of donor–acceptor cyclopropanes was also been developed. The mechanisms of the discovered reactions involving the formation of a comparatively stable 1,2‐ylide intermediate have been studied. Old ring, new reactivity: A new type of donor–acceptor cyclopropane reactivity has been discovered. On treatment with anhydrous GaCl3, they react as sources of even‐numbered 1,2‐ and 1,4‐dipoles instead of the classical odd‐numbered 1,3‐dipoles owing to the migration of positive charge from the benzyl center.
AbstractList	A new type of donor-acceptor cyclopropane reactivity has been discovered. On treatment with anhydrous GaCl3, they react as sources of even-numbered 1,2- and 1,4-dipoles instead of the classical odd-numbered 1,3-dipoles due to migration of positive charge from the benzyl center. This type of reactivity has been demonstrated for new reactions, namely, cyclodimerizations of donor-acceptor cyclopropanes that occur as [2+2]-, [3+2]-, [4+2]-, [5+2]-, [4+3]-, and [5+4]-annulations. The [4+2]-annulation of 2-arylcyclopropane-1,1-dicarboxylates to give polysubstituted 2-aryltetralins has been developed in a preparative version that provides exceedingly high regio- and diastereoselectivity and high yields. The strategy for selective hetero-combination of donor-acceptor cyclopropanes was also been developed. The mechanisms of the discovered reactions involving the formation of a comparatively stable 1,2-ylide intermediate have been studied. [PUBLICATION ABSTRACT] A new type of donor–acceptor cyclopropane reactivity has been discovered. On treatment with anhydrous GaCl 3 , they react as sources of even‐numbered 1,2‐ and 1,4‐dipoles instead of the classical odd‐numbered 1,3‐dipoles due to migration of positive charge from the benzyl center. This type of reactivity has been demonstrated for new reactions, namely, cyclodimerizations of donor–acceptor cyclopropanes that occur as [2+2]‐, [3+2]‐, [4+2]‐, [5+2]‐, [4+3]‐, and [5+4]‐annulations. The [4+2]‐annulation of 2‐arylcyclopropane‐1,1‐dicarboxylates to give polysubstituted 2‐aryltetralins has been developed in a preparative version that provides exceedingly high regio‐ and diastereoselectivity and high yields. The strategy for selective hetero‐combination of donor–acceptor cyclopropanes was also been developed. The mechanisms of the discovered reactions involving the formation of a comparatively stable 1,2‐ylide intermediate have been studied. A new type of donor-acceptor cyclopropane reactivity has been discovered. On treatment with anhydrous GaCl3 , they react as sources of even-numbered 1,2- and 1,4-dipoles instead of the classical odd-numbered 1,3-dipoles due to migration of positive charge from the benzyl center. This type of reactivity has been demonstrated for new reactions, namely, cyclodimerizations of donor-acceptor cyclopropanes that occur as [2+2]-, [3+2]-, [4+2]-, [5+2], [4+3]-, and [5+4]-annulations. The [4+2]-annulation of 2-arylcyclopropane-1,1-dicarboxylates to give polysubstituted 2-aryltetralins has been developed in a preparative version that provides exceedingly high regio- and diastereoselectivity and high yields. The strategy for selective hetero-combination of donor-acceptor cyclopropanes was also been developed. The mechanisms of the discovered reactions involving the formation of a comparatively stable 1,2-ylide intermediate have been studied. A new type of donor-acceptor cyclopropane reactivity has been discovered. On treatment with anhydrous GaCl sub(3), they react as sources of even-numbered 1,2- and 1,4-dipoles instead of the classical odd-numbered 1,3-dipoles due to migration of positive charge from the benzyl center. This type of reactivity has been demonstrated for new reactions, namely, cyclodimerizations of donor-acceptor cyclopropanes that occur as [2+2]-, [3+2]-, [4+2]-, [5+2]-, [4+3]-, and [5+4]-annulations. The [4+2]-annulation of 2-arylcyclopropane-1,1-dicarboxylates to give polysubstituted 2-aryltetralins has been developed in a preparative version that provides exceedingly high regio- and diastereoselectivity and high yields. The strategy for selective hetero-combination of donor-acceptor cyclopropanes was also been developed. The mechanisms of the discovered reactions involving the formation of a comparatively stable 1,2-ylide intermediate have been studied. Old ring, new reactivity: A new type of donor-acceptor cyclopropane reactivity has been discovered. On treatment with anhydrous GaCl sub(3), they react as sources of even-numbered 1,2- and 1,4-dipoles instead of the classical odd-numbered 1,3-dipoles owing to the migration of positive charge from the benzyl center. A new type of donor–acceptor cyclopropane reactivity has been discovered. On treatment with anhydrous GaCl3, they react as sources of even‐numbered 1,2‐ and 1,4‐dipoles instead of the classical odd‐numbered 1,3‐dipoles due to migration of positive charge from the benzyl center. This type of reactivity has been demonstrated for new reactions, namely, cyclodimerizations of donor–acceptor cyclopropanes that occur as [2+2]‐, [3+2]‐, [4+2]‐, [5+2]‐, [4+3]‐, and [5+4]‐annulations. The [4+2]‐annulation of 2‐arylcyclopropane‐1,1‐dicarboxylates to give polysubstituted 2‐aryltetralins has been developed in a preparative version that provides exceedingly high regio‐ and diastereoselectivity and high yields. The strategy for selective hetero‐combination of donor–acceptor cyclopropanes was also been developed. The mechanisms of the discovered reactions involving the formation of a comparatively stable 1,2‐ylide intermediate have been studied. Old ring, new reactivity: A new type of donor–acceptor cyclopropane reactivity has been discovered. On treatment with anhydrous GaCl3, they react as sources of even‐numbered 1,2‐ and 1,4‐dipoles instead of the classical odd‐numbered 1,3‐dipoles owing to the migration of positive charge from the benzyl center.
Author	Timofeev, Vladimir P. Novikov, Roman A. Korolev, Victor A. Tarasova, Anna V. Tomilov, Yury V.
Author_xml	– sequence: 1 givenname: Roman A. surname: Novikov fullname: Novikov, Roman A. organization: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow (Russian Federation) – sequence: 2 givenname: Anna V. surname: Tarasova fullname: Tarasova, Anna V. organization: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow (Russian Federation) – sequence: 3 givenname: Victor A. surname: Korolev fullname: Korolev, Victor A. organization: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow (Russian Federation) – sequence: 4 givenname: Vladimir P. surname: Timofeev fullname: Timofeev, Vladimir P. organization: V. A. Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, 32 Vavilov st., 119991 Moscow (Russian Federation) – sequence: 5 givenname: Yury V. surname: Tomilov fullname: Tomilov, Yury V. email: tom@ioc.ac.ru organization: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow (Russian Federation)
BackLink	https://www.ncbi.nlm.nih.gov/pubmed/24554497$$D View this record in MEDLINE/PubMed
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Copyright	2014 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
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Keywords	carbocycles donor-acceptor systems cyclodimerization annulation lewis acids
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Notes	Russian Federation President Council for Grants - No. NSh-604.2012.3 istex:B99E206F4A102A2E0C71EFF331E22773720AAB31 ArticleID:ANIE201306186 This work was supported by the Russian Federation President Council for Grants (Program for State Support of Leading Scientific Schools of the Russian Federation, grant no. NSh-604.2012.3), the Division of Chemistry and Materials Sciences of the Russian Academy of Sciences (Program for Basic Research "Theoretical and Experimental Study of the Nature of Chemical Bonds and Mechanisms of Important Chemical Reactions and Processes") and the Program "Molecular and cell Biology " of the Presidium of the Russian Academy of Sciences. ark:/67375/WNG-SJHQCMVT-B This work was supported by the Russian Federation President Council for Grants (Program for State Support of Leading Scientific Schools of the Russian Federation, grant no. NSh‐604.2012.3), the Division of Chemistry and Materials Sciences of the Russian Academy of Sciences (Program for Basic Research “Theoretical and Experimental Study of the Nature of Chemical Bonds and Mechanisms of Important Chemical Reactions and Processes”) and the Program “Molecular and cell Biology ” of the Presidium of the Russian Academy of Sciences. ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
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Snippet	A new type of donor–acceptor cyclopropane reactivity has been discovered. On treatment with anhydrous GaCl3, they react as sources of even‐numbered 1,2‐ and... A new type of donor-acceptor cyclopropane reactivity has been discovered. On treatment with anhydrous GaCl3 , they react as sources of even-numbered 1,2- and... A new type of donor–acceptor cyclopropane reactivity has been discovered. On treatment with anhydrous GaCl 3 , they react as sources of even‐numbered 1,2‐ and... A new type of donor-acceptor cyclopropane reactivity has been discovered. On treatment with anhydrous GaCl3, they react as sources of even-numbered 1,2- and... A new type of donor-acceptor cyclopropane reactivity has been discovered. On treatment with anhydrous GaCl sub(3), they react as sources of even-numbered 1,2-...
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SubjectTerms	annulation carbocycles Charge cyclodimerization Cyclopropane donor-acceptor systems Formations lewis acids Migration Strategy
Title	A New Type of Donor-Acceptor Cyclopropane Reactivity: The Generation of Formal 1,2- and 1,4-Dipoles
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