Incorporation of an allene unit into 1,4-dihydronaphthalene: generation of 1,2-benzo-1,4,5-cycloheptatriene and its dimerization

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dc.authorid0000-0002-0720-2735
dc.authorid0000-0002-5098-1842
dc.contributor.authorAzizoglu, Akin
dc.contributor.authorDemirkol, Onur
dc.contributor.authorKilic, Turgut
dc.contributor.authorYildiz, Y. Kemal
dc.date.accessioned2019-08-01T13:38:39Z
dc.date.available2019-08-01T13:38:39Z
dc.date.issued2007
dc.departmentNiğde ÖHÜ
dc.description.abstract1-Bromo-1-fluoro-[1a,2,7,7a]-tetrahydro-1H-cyclopropa[b]naphthalene (19) has been prepared by the addition of bromolluoro-carbene to 1,4-dihydronaphthalene (18). Treatment of a solution of 19 in dry ether with MeLi afforded the tricyclic hydrocarbon 17, resulting from the intramolecular C-H insertion of carbene 16, and two dimerization products, the head-to-head 20 and head-to-tail 21 allene dimers, confirming the formation of title cycloallene 15 as a reactive intermediate. B3LYP/6-31 G(d) calculation predicts the activation barriers for insertion product 17 and allene product 15 as 3.70 and 9.52 kcal/mol, respectively. This prediction was in good agreement with our experimental results. (c) 2007 Elsevier Ltd. All rights reserved.
dc.identifier.doi10.1016/j.tet.2007.01.017
dc.identifier.endpage2413
dc.identifier.issn0040-4020
dc.identifier.issue11
dc.identifier.scopus2-s2.0-33846821951
dc.identifier.scopusqualityQ2
dc.identifier.startpage2409
dc.identifier.urihttps://dx.doi.org/10.1016/j.tet.2007.01.017
dc.identifier.urihttps://hdl.handle.net/11480/5404
dc.identifier.volume63
dc.identifier.wosWOS:000244732800004
dc.identifier.wosqualityQ1
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.institutionauthor[0-Belirlenecek]
dc.language.isoen
dc.publisherPERGAMON-ELSEVIER SCIENCE LTD
dc.relation.ispartofTETRAHEDRON
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.subjectcyclic allenes
dc.subjectcarbenes
dc.subjectrearrangements
dc.subjectDFT calculations
dc.titleIncorporation of an allene unit into 1,4-dihydronaphthalene: generation of 1,2-benzo-1,4,5-cycloheptatriene and its dimerization
dc.typeArticle

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