title: Bicyclo[3.2.1]octane synthons from cyclopropenes: functionalization of cycloadducts by nucleophilic additions.
abstract: It has been known for several decades that a highly functionalized family of tetrahalobicyclo[3.2.1]octadienes are readily available through the cycloaddition of furan or cyclopentadiene with either tetrachloro- or tetrabromocyclopropene. However, the application of these highly functionalized building blocks in synthesis has remained relatively unexplored in relation to their better-known counterparts derived through oxyallyl cation additions. As a first step toward utilizing these highly versatile intermediates in synthesis, a study of the addition of various nucleophiles to the halogenated nucleus has been conducted. It has been found that these halogenated systems are amenable to a wide range of functionalizations in high yields and with good selectivities.
authors.affiliation: Department of Chemistry, University of Florida, Gainesville, Florida 32611, USA.
authors.forename: Ravi S
authors.initials: RS
authors.lastname: Orugunty
authors.forename: Dennis L
authors.initials: DL
authors.lastname: Wright
authors.forename: Merle A
authors.initials: MA
authors.lastname: Battiste
authors.forename: Richard J
authors.initials: RJ
authors.lastname: Helmich
authors.forename: Khalil
authors.initials: K
authors.lastname: Abboud