title: Enabling the synthesis of perfluoroalkyl bicyclobutanes via 1,3 γ-silyl elimination.
abstract: Two new bicyclobutanes were prepared from cyclobutyl systems by a novel, solvolytic, carbocation-based methodology. An electron-withdrawing perfluoroalkyl group at the incipient cationic center enhances neighboring-group participation of the γ-silyl group, inducing facile, remarkably selective 1,3-elimination yielding only bicyclobutanes. The method unlocks potential access to a host of EWG-substituted strained rings and a potential new method for the synthesis of trifluoromethylcyclopropanes.
authors.affiliation: Department of Chemistry, Stonehill College, 320 Washington Street, Easton, Massachusetts 02357, United States.
authors.forename: Christopher B
authors.initials: CB
authors.lastname: Kelly
authors.forename: Allison M
authors.initials: AM
authors.lastname: Colthart
authors.forename: Brad D
authors.initials: BD
authors.lastname: Constant
authors.forename: Sean R
authors.initials: SR
authors.lastname: Corning
authors.forename: Lily N E
authors.initials: LN
authors.lastname: Dubois
authors.forename: Jacqueline T
authors.initials: JT
authors.lastname: Genovese
authors.forename: Julie L
authors.initials: JL
authors.lastname: Radziewicz
authors.forename: Ellen M
authors.initials: EM
authors.lastname: Sletten
authors.forename: Katherine R
authors.initials: KR
authors.lastname: Whitaker
authors.forename: Leon J
authors.initials: LJ
authors.lastname: Tilley