title: Formation of 3-halobenzyne: solvent effects and cycloaddition adducts.
abstract: Noncoordinating solvents permit the halogen-metal exchange-induced formation of benzyne (aryne) from di- and trihalobenzene precursors in the presence of cyclopentadiene to give 1,4-dihydro-1,4-methano-naphthalenes. Studies with mixed halide precursors and nonacidic Diels-Alder diene traps reveal that ethereal and hydrocarbon solvents influence the halide leaving group facility, resulting in a reversal of 3-halobenzyne regioselectivity.
authors.affiliation: Pfizer Global Research and Development, Groton Laboratories, Pfizer, Inc, Groton, Connecticut 06340, USA. coejw@groton.pfizer.com
authors.forename: Jotham W
authors.initials: JW
authors.lastname: Coe
authors.forename: Michael C
authors.initials: MC
authors.lastname: Wirtz
authors.forename: Crystal G
authors.initials: CG
authors.lastname: Bashore
authors.forename: John
authors.initials: J
authors.lastname: Candler