title: Corner Bromination of 2-Methyl-endo-tricyclo[3.2.1.0(2,4)]octane and -oct-6-ene.
abstract: Reaction of 2-methyl-endo-tricyclo[3.2.1.0(2,4)]octane (1) with bromine in CCl(4) gave 2-exo,3-endo-dibromo-2-endo-methylbicyclo[3.2.1]octane (3) which rearranges on silica to 2-exo,6-endo-dibromo-1-methylbicyclo[2.2.2]octane (4). Reaction in methanol gave 4-endo-bromo-2-exo-methoxy-2-endo-methylbicyclo[3.2.1]octane (10) and 4-endo-bromo-2-endo-methoxy-2-exo-methylbicyclo[3.2.1]octane (11) formed by corner attack of the bromine electrophile with C2-C4 bond rupture and inversion of configuration at the site of electrophilic attack. Reaction of 2-methyl-endo-tricyclo[3.2.1.0(2,4)]oct-6-ene (2) with bromine in CCl(4) and methanol gave products of reaction at the alkene site.
authors.affiliation: Department of Chemistry, Texas Christain University, Fort Worth, Texas 76129.
authors.forename: Andrew
authors.initials: A
authors.lastname: Burritt
authors.forename: James M.
authors.initials: JM
authors.lastname: Coxon
authors.forename: Peter J.
authors.initials: PJ
authors.lastname: Steel
authors.forename: William B.
authors.initials: WB
authors.lastname: Smith