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dc.contributor.authorBerkil Akar, Kıymet
dc.contributor.authorÇakmak, Osman
dc.contributor.authorTunç, Tuncay
dc.date.accessioned2019-06-18T11:21:35Z
dc.date.available2019-06-18T11:21:35Z
dc.date.issued2016en_US
dc.identifier.issn1300-0527
dc.identifier.urihttp://dx.doi.org/10.3906/kim-1506-28
dc.identifier.urihttps://hdl.handle.net/20.500.12451/1398
dc.descriptionTunç, Tuncay (Aksaray, Yazar)en_US
dc.description.abstractRegio- and stereoselective synthesis are described for convenient preparation of hydroxy- and methoxynaph-thalenes starting from naphthalene (1).cis,cis,trans-2,3,5,8-Tetrabromo-4-methoxy-1,2,3,4-tetrahydronaphthalen-1-ol(6),cis,cis,trans-2,3,5,8-tetrabromo-1,4-dimethoxy-1,2,3,4-tetrahydronaphthalene (7), andcis,cis,cis-2,3,5,8-tetrabromo-1,4-dimethoxy-1,2,3,4-tetrahydronaphthalene (8) were obtained with silver-induced substitution oftrans,cis,trans-1,2,3,4,5,8-hexabromo-1,2,3,4-tetrahydronaphthalene (3). Base-promoted aromatization of dimethoxides7and8afforded3,5,8-tribromo-1-methoxynaphthalene (9) and 2,5,8-tribromo-1-methoxynaphthalene (10). The reaction of6withsodium methoxide formed compounds10and 3,5,8-tribromonaphthalen-1-ol (16). Bromination of9and16withBr2in dichloromethane at room temperature produced 2,3,5,8-tetrabromo-1-methoxynaphthalene (14) and 2,3,4,5,8-pentabromonaphthalen-1-ol (18), respectively, while compound10did not react in the same conditions. Pyridine-inducedelimination of hexabromide3afforded 1,4,6-tribromnaphthalene (21) in 99% yield and thermolysis of the hexabromide3gave mainly 1,4,6,7-tetrabromonaphthalene (22). Tetrabromide22was transformed to 1,4,6,7-tetramethoxynaphthalene(23) by copper-assisted nucleophilic substitution reaction.en_US
dc.description.abstract...en_US
dc.language.isoengen_US
dc.publisherTÜBİTAKen_US
dc.relation.isversionof10.3906/kim-1506-28en_US
dc.rightsinfo:eu-repo/semantics/openAccessen_US
dc.subjectMethoxynaphthaleneen_US
dc.subjectSilver-İnduced Substitutionen_US
dc.subjectBase-Promoted Eliminationen_US
dc.subjectHydroxynaphthaleneen_US
dc.subjectBromonaphthaleneen_US
dc.subject...en_US
dc.titlePolybrominated methoxy- and hydroxynaphthalenesen_US
dc.typearticleen_US
dc.relation.journalTurkish Journal of Chemistryen_US
dc.contributor.departmentEğitim Fakültesien_US
dc.identifier.volume40en_US
dc.identifier.issue2en_US
dc.identifier.startpage332en_US
dc.identifier.endpage346en_US
dc.relation.publicationcategoryMakale - Ulusal Hakemli Dergi - Kurum Öğretim Elemanıen_US


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