title: Bridged synthons from tetrabromocyclopropene: studies on the rearrangement of the primary Diels-Alder adduct with 2,5-dimethylfuran.
abstract: The reaction of tetrabromocyclopropene and furan leads directly to 8-oxabicyclo[3.2.1]octadiene derivatives. It has been proposed that this involves an initial Diels-Alder reaction followed by rearrangement of the primary adduct. We have, for the first time, isolated a primary adduct and established through X-ray crystallographic analysis that the adduct is the product of an exo-selective addition. Kinetic studies suggest the intermediacy of charged intermediates during the rearrangement.
authors.affiliation: Department of Chemistry, University of Florida, Gainesville, Florida 32606, USA.
authors.forename: Ravi S
authors.initials: RS
authors.lastname: Orugunty
authors.forename: Ion
authors.initials: I
authors.lastname: Ghiviriga
authors.forename: Khalil A
authors.initials: KA
authors.lastname: Abboud
authors.forename: Merle A
authors.initials: MA
authors.lastname: Battiste
authors.forename: Dennis L
authors.initials: DL
authors.lastname: Wright