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

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dc.contributor.authorAltundaş, Ramazan
dc.contributor.authorDaştan, Arif
dc.contributor.authorÜnaldi, Nermin S.
dc.contributor.authorGüven, Kutalmış
dc.contributor.authorUzun, Orhan
dc.contributor.authorBalcı, Metin
dc.date.accessioned2020-06-25T15:13:17Z
dc.date.available2020-06-25T15:13:17Z
dc.date.issued2002
dc.departmentKırıkkale Üniversitesi
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-?-methane rearrangement products. However, methyl 3-cyano-2-benzobarrelenecarboxylate (17) underwent an intramolecular [2? + 2?] cycloaddition reaction, whilst methyl 3-cyano-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 destabilizing 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.issn1434193X
dc.identifier.issue3en_US
dc.identifier.scopus2-s2.0-0036172038
dc.identifier.scopusqualityQ2
dc.identifier.startpage526en_US
dc.identifier.urihttps://doi.org/10.1002/1099-0690(20022)2002:3<526
dc.identifier.urihttps://hdl.handle.net/20.500.12587/1707
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherWiley-VCH Verlagen_US
dc.relation.ispartofEuropean Journal of Organic Chemistry
dc.relation.publicationcategoryMakale - Ulusal Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectBenzobarreleneen_US
dc.subjectBenzonorbornadieneen_US
dc.subjectDi-?-methane rearrangementen_US
dc.subjectPhotolysisen_US
dc.titleThe Di-π-methane Photorearrangement of 2,3-Disubstituted Benzobarrelenesand Benzonorbornadiene 2 Substituent Effects in Regioselectivityen_US
dc.typeArticle

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