title: A different route to the synthesis of 9,10-disubstituted phenanthrenes.
abstract: We here report the synthesis of 10-aryl-9-hydroxy- and 10-aryl-9-aminophenanthrenes by reaction of the anions of 9-phenanthrol and 9-aminophenanthrene, respectively, with aryl halides (iodobenzene, 4-iodoanisole, 9-bromophenantrene). Good yields of 9,10-disubstituted phenanthrenes were obtained in these reactions (>75% and approximately 50% for the 9-amino and 9-hydroxyphenanthrene rings, respectively). Extension of the procedure to the reaction of both anions with o-dihalobenzenes leads to the synthesis of the ring closure products (aza- or oxa-indeno[1,2-l]phenanthrene), which bear a pentacyclic aromatic condensed ring system, although in lower overall yields (approximately 35%).
authors.affiliation: INFIQC, Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Ciudad Universitaria, 5000 Córdoba, Argentina.
authors.forename: Tomás C
authors.initials: TC
authors.lastname: Tempesti
authors.forename: Adriana B
authors.initials: AB
authors.lastname: Pierini
authors.forename: María T
authors.initials: MT
authors.lastname: Baumgartner