title: The Unexpected Formation of 9,9,10,10-Tetrafluoro-1,2,4,12-tetraphenyl[2.2]paracyclophan-1-ene.
abstract: An investigation of the palladium-catalyzed Kumada cross-coupling reaction between PhMgBr and (pseudo-ortho) 4,12-diiodo-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane revealed that in addition to the expected cross-coupled product, an unintended major product was generated. The product was determined to be 9,9,10,10-tetrafluoro-1,2,4,12-tetraphenyl[2.2]paracyclophan-1-ene by X-ray crystallography and is proposed to be formed via the first reported example of reductive defluorination by a Grignard reagent.
authors.affiliation: †Department of Chemistry, Rutgers, The State University of New Jersey, 315 Penn Street, Camden, New Jersey 08102-1411, United States.
authors.forename: Alex J
authors.initials: AJ
authors.lastname: Roche
authors.affiliation: ‡Department of Chemistry, University of Florida, Gainesville, Florida 32611-7200, United States.
authors.forename: Khalil A
authors.initials: KA
authors.lastname: Abboud
authors.affiliation: ‡Department of Chemistry, University of Florida, Gainesville, Florida 32611-7200, United States.
authors.forename: William R
authors.initials: WR
authors.lastname: Dolbier