The Di-π-methane Photorearrangement of 2,3-Disubstituted Benzobarrelenes and Benzonorbornadiene − Substituent Effects in Regioselectivity

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dc.contributor.authorAltundaş, R.
dc.contributor.authorDastan, A.
dc.contributor.authorÜnaldi, N.S.
dc.contributor.authorGüven, K.
dc.contributor.authorUzun, O.
dc.contributor.authorBalci, M.
dc.date.accessioned2020-06-25T17:35:07Z
dc.date.available2020-06-25T17:35:07Z
dc.date.issued2002
dc.departmentKırıkkale Üniversitesi
dc.descriptionUZUN, ORHAN/0000-0001-7586-9075; Dastan, Arif/0000-0002-9577-2251
dc.description.abstract2,3-Disubstituted benzobarrelene and benzonorbornadiene derivatives 16, 17, and 18, containing electron-withdrawing and electron-donating substituents, have been synthesized and subjected to triplet-sensitized photoisomerization. Methyl 3-methyl-2-benzobarrelenecarboxylate (16) gave two di-pi-methane rearrangement products. However, methyl 3-cyano-2-benzobarrelenecarboxyidte (17) underwent an intramolecular [2(pi) + 2(pi)] cycloaddition reaction, whilst methyl 3cyano-2-benzonorbornadienecarboxylate (18) formed dimer 40. The formation of these products is discussed in terms of the radical stabilizing effect of the substituents and the destabitizing effect on the formation of cyclopropane ring.en_US
dc.identifier.citationclosedAccessen_US
dc.identifier.doi10.1002/1099-0690(20022)2002:3<526
dc.identifier.endpage533en_US
dc.identifier.issn1434-193X
dc.identifier.issn1099-0690
dc.identifier.issue3en_US
dc.identifier.startpage526en_US
dc.identifier.urihttps://doi.org/10.1002/1099-0690(20022)2002:3<526
dc.identifier.urihttps://hdl.handle.net/20.500.12587/3026
dc.identifier.volume2002en_US
dc.identifier.wosWOS:000173694500016
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.language.isoen
dc.publisherWiley-V C H Verlag Gmbhen_US
dc.relation.ispartofEuropean Journal Of Organic Chemistry
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectbenzobarreleneen_US
dc.subjectbenzonorbornadieneen_US
dc.subjectdi-pi-methane rearrangementen_US
dc.subjectphotolysisen_US
dc.titleThe Di-π-methane Photorearrangement of 2,3-Disubstituted Benzobarrelenes and Benzonorbornadiene − Substituent Effects in Regioselectivityen_US
dc.typeArticle

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