title: Remarkable efficiency of the aryne chemistry of (dehydro)octafluoro[2.2]paracyclophane when using the Cadogan method.
abstract: Generation of the aryne, (dehydro)octafluoro[2.2]paracyclophane, from its acetamide derivative utilizing the Cadogan method led to remarkable results with respect to Diels-Alder and ene reactivity. A comparison was made between this new and virtually unused method and our earlier reported results using Cram methodology (reaction of aryl iodide with potassium tert-butoxide). Surprisingly, no ene reactivity was observed with the Cram methodology. This mechanistic conundrum was examined extensively with no unambiguous explanation for the difference in reactivity being found.
authors.affiliation: Department of Chemistry, University of Florida, P.O. Box 117200, Gainesville, Florida 32611-7200, USA. wrd@chem.ufl.edu
authors.forename: William R
authors.initials: WR
authors.lastname: Dolbier
authors.forename: Yi-An
authors.initials: YA
authors.lastname: Zhai
authors.forename: Will
authors.initials: W
authors.lastname: Wheelus
authors.forename: Merle A
authors.initials: MA
authors.lastname: Battiste
authors.forename: Ion
authors.initials: I
authors.lastname: Ghiviriga
authors.forename: Michael D
authors.initials: MD
authors.lastname: Bartberger