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

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.