title: 4,5-dehydro- and 4,5,15,16-bis(dehydro)octafluoro[2.2]paracyclophanes: facile generation and extraordinary Diels-Alder reactivity.
abstract: Dehydroiodination of 4-iodo- and 4,15-diiodo-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane by treatment with KO(t)Bu in the presence of benzene, naphthalene, anthracene, and [2.2]paracyclophane affords each of the corresponding Diels-Alder mono- and bis-cycloadducts derived from the presumed aryne intermediates in high yield. Monoadducts of t-butylbenzene and furan are also obtained in excellent yield. All of the products were characterized by their NMR spectra, with four of them also being confirmed by X-ray crystallography. The extraordinary selectivity/reactivity of the aryne intermediate is discussed.
authors.affiliation: Department of Chemistry, University of Florida, P.O. Box 117200, Gainesville, FL 32611-7200, USA.
authors.forename: Merle A
authors.initials: MA
authors.lastname: Battiste
authors.forename: Jian-Xin
authors.initials: JX
authors.lastname: Duan
authors.forename: Yi-An
authors.initials: YA
authors.lastname: Zhai
authors.forename: Ion
authors.initials: I
authors.lastname: Ghiviriga
authors.forename: Khalil A
authors.initials: KA
authors.lastname: Abboud
authors.forename: William R
authors.initials: WR
authors.lastname: Dolbier