title: Type 1 ring-opening reactions of cyclopropanated 7-oxabenzonorbornadienes with organocuprates.
abstract: For the first time, nucleophilic ring-openings of cyclopropanated 7-oxabenzonorbornadiene were investigated, providing a novel approach to the preparation of 2-methyl-1,2-dihydronaphthalen-1-ols. Satisfactory yields (up to 95%) were achieved using n-Bu2CuCNLi2 as the nucleophile and Et2O as the solvent. The reaction demonstrated successful incorporation of primary, secondary, tertiary and aromatic nucleophiles, as well as ring-openings of substrates bearing arene substituents and C1-bridgehead substituents. A generalized mechanism for these transformations is also proposed.
authors.affiliation: Guelph-Waterloo Centre for Graduate Work in Chemistry and Biochemistry, Department of Chemistry, University of Guelph , Guelph, Ontario, Canada N1G 2W1.
authors.forename: Emily
authors.initials: E
authors.lastname: Carlson
authors.forename: Jamie
authors.initials: J
authors.lastname: Haner
authors.forename: Mary
authors.initials: M
authors.lastname: McKee
authors.forename: William
authors.initials: W
authors.lastname: Tam