Polybrominated methoxy- and hydroxynaphthalenes
| dc.contributor.author | Berkil Akar, Kıymet | |
| dc.contributor.author | Çakmak, Osman | |
| dc.contributor.author | Tunç, Tuncay | |
| dc.date.accessioned | 2019-06-18T11:21:35Z | |
| dc.date.available | 2019-06-18T11:21:35Z | |
| dc.date.issued | 2016 | |
| dc.department | Eğitim Fakültesi | |
| dc.description | Tunç, Tuncay (Aksaray, Yazar) | |
| dc.description.abstract | Regio- 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. | |
| dc.description.abstract | ... | |
| dc.identifier.doi | 10.3906/kim-1506-28 | |
| dc.identifier.endpage | 346 | en_US |
| dc.identifier.issn | 1300-0527 | |
| dc.identifier.issue | 2 | en_US |
| dc.identifier.scopusquality | Q3 | |
| dc.identifier.startpage | 332 | en_US |
| dc.identifier.uri | http://dx.doi.org/10.3906/kim-1506-28 | |
| dc.identifier.uri | https://hdl.handle.net/20.500.12451/1398 | |
| dc.identifier.volume | 40 | en_US |
| dc.identifier.wosquality | N/A | |
| dc.indekslendigikaynak | Web of Science | |
| dc.indekslendigikaynak | Scopus | |
| dc.indekslendigikaynak | TR-Dizin | |
| dc.language.iso | en | |
| dc.publisher | TÜBİTAK | |
| dc.relation.ispartof | Turkish Journal of Chemistry | |
| dc.relation.publicationcategory | Makale - Ulusal Hakemli Dergi - Kurum Öğretim Elemanı | |
| dc.rights | info:eu-repo/semantics/openAccess | |
| dc.subject | Methoxynaphthalene | |
| dc.subject | Silver-İnduced Substitution | |
| dc.subject | Base-Promoted Elimination | |
| dc.subject | Hydroxynaphthalene | |
| dc.subject | Bromonaphthalene | |
| dc.subject | ... | |
| dc.title | Polybrominated methoxy- and hydroxynaphthalenes | |
| dc.type | Article |
