Synthesis of hydroxy, epoxy, nitrato and methoxy derivatives of tetralins and naphthalenes

Erenler R., Demirtas İ., Buyukkidan B., Cakmak O.

Journal of Chemical Research, no.12, pp.753-757, 2006 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Publication Date: 2006
  • Doi Number: 10.3184/030823406780199721
  • Journal Name: Journal of Chemical Research
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.753-757
  • Keywords: 1,4-dihydroxy-2,3-dibromotetralins, 1,4-dinitrato-2,3- dibromotetralins, Arene oxides, Tetralin and naphthalene derivatives
  • Ondokuz Mayıs University Affiliated: No

Abstract

Stereoselective syntheses are described for cis,trans,cis-2,3,5-tribromo-1, 4-dihydroxytetralin, trans,trans,cis-2,3,5-tribromo-1,4-dihydroxytetralin, trans,trans,trans-1,4-dihydroxy-2,3-dibromotetralin, trans,trans,trans-1- hydroxy-2,3,4-tribromotetralin, cis,cis,cis-1,2-epoxy-3,5-dibromo-4- hydroxytetralin, anti-1,2:3,4-diepoxytetralin, 1-hydroxy-4-bromonaphthalene, trans,trans,trans-1,4-dinitrato-2,3-dibromotetralin, 1-nitrato-2,3,4- tribromotetralin, 2,3-dibromonaphthalene and 1-methoxy-4-nitrato-2,3- dibromonaphthalene. These isomeric arene oxides and disubstituted naphthalenes provide excellent precursors for a number of 1,4- and 2,3-disubstituted naphthalene derivatives that are difficult to prepare using other routes. The structures of the naphthalene and tetralin derivatives were assigned by NMR and other techniques.