Polybrominated methoxy- and hydroxynaphthalenes
Yazarlar (3)
Doç. Dr. Kıymet BERKİL AKAR
Tokat Gaziosmanpaşa Üniversitesi, Türkiye
İstanbul Gelişim Üniversitesi, Türkiye
Aksaray Üniversitesi, Türkiye
| Makale Türü | Özgün Makale |
| Makale Alt Türü | SSCI, AHCI, SCI, SCI-Exp dergilerinde yayınlanan tam makale |
| Dergi Adı | Turkish Journal of Chemistry |
| Dergi ISSN | 1300-0527 Wos Dergi Scopus Dergi |
| Dergi Tarandığı Indeksler | SCI-Expanded |
| Dergi Grubu | Q4 |
| Makale Dili | İngilizce |
| Basım Tarihi | 01-2016 |
| Cilt No | 40 |
| Sayı | 2 |
| Sayfalar | 332 / 346 |
| DOI Numarası | 10.3906/kim-1506-28 |
| Makale Linki | http://dx.doi.org/10.3906/kim-1506-28 |
| Özet |
| 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. |
| Anahtar Kelimeler |
| Base-promoted elimination | Bromonaphthalene | Hydroxynaphthalene | Methoxynaphthalene | Silver-induced substitution |
BM Sürdürülebilir Kalkınma Amaçları
| Atıf Sayıları | |
| SCOPUS | 1 |
| Google Scholar | 1 |