Bromination of tetralin. Short and efficient synthesis of 1,4-dibromonaphthalene
Collection of Czechoslovak Chemical Communications, cilt.65, sa.11, ss.1791-1804, 2000 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 65 Sayı: 11
- Basım Tarihi: 2000
- Doi Numarası: 10.1135/cccc20001791
- Dergi Adı: Collection of Czechoslovak Chemical Communications
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
- Sayfa Sayıları: ss.1791-1804
- Anahtar Kelimeler: Aromatic nucleophilic substitution, Bromination, Bromine, Halogenation, Naphthalenes, Photobromination, Tetralin
- Ondokuz Mayıs Üniversitesi Adresli: Hayır
Özet
High-temperature bromination of tetralin (1,2,3,4-tetrahydronaphthalene) with bromine resulted in benzylic biomination to give 1,4-dibromo-1,2,3,4-tetrahydronaphthalene (4) as a major product and several secondary products. Photolytic bromination of tetralin and subsequent double dehydrobromination of 1,1,4,4-tetrabromo-1,2,3,4-tetrahydronaphthalene (10) gave 1,4-dibromonaphthalene (11) as the sole product in a high yield. 1,4-Dibromonaphthalene is efficiently converted to the corresponding methoxy (12 and 13) and cyano (14 and 15) derivatives of naphthalene.