title: Nucleophilic substitution of bromonorbornenes and derivatives by electron transfer reactions.
abstract: The photoinitiated substitution reactions of anti-7-bromobenzonorbornadiene (5), its syn isomer 6, exo-anti-13-bromobenzocyclobutanorbornene (7), syn-7-bromonorbornene (8) and bromonorbornane (9) with Me(3)Sn(-) and Ph(2)P(-) anions, in liquid ammonia, are here informed to occur with good yields of substitution. The stereochemical outcome is discussed in terms of calculations with the B3LYP functional and the 6-31+G* basis set; the solvent being included as a continuum through the PCM model. The experimental relative chemical reactivity of pairs of substrates toward a given anion is also presented.
authors.affiliation: INFIQC, Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Ciudad Universitaria, 5000 Córdoba, Argentina.
authors.forename: Karina F
authors.initials: KF
authors.lastname: Crespo Andrada
authors.forename: Lucas E
authors.initials: LE
authors.lastname: Peisino
authors.forename: Murat
authors.initials: M
authors.lastname: Güney
authors.forename: Arif
authors.initials: A
authors.lastname: Daştan
authors.forename: Adriana B
authors.initials: AB
authors.lastname: Pierini