title: Photostimulated reactions of phenylacetic acid dianions with aryl halides. Influence of the metallic cation on the regiochemistry of arylation.
abstract: [reaction: see text]Phenylacetic acid dianions react via what appears to be an S(RN)1 process with aryl halides under photostimulation to afford aryl substitution products 5 and 6. When the counterion is K+, only 4-biphenylacetic acids 5 are obtained. Both alpha- and para-coupling occurs with Na+ to give a mixture of 5 and 6, while exclusive formation of diphenylacetic acids 6 is observed with the dilithio salt of 1.
authors.affiliation: Hampton University, Department of Chemistry, VA 23668, USA.
authors.forename: G C
authors.initials: GC
authors.lastname: Nwokogu
authors.forename: J W
authors.initials: JW
authors.lastname: Wong
authors.forename: T D
authors.initials: TD
authors.lastname: Greenwood
authors.forename: J F
authors.initials: JF
authors.lastname: Wolfe
mesh_terms: D003500:Cyclization; D009682:Magnetic Resonance Spectroscopy; D008670:Metals / Q000737:chemistry*; D010648:Phenylacetates / Q000737:chemistry* / Q000528:radiation effects; D010777:Photochemistry; D014466:Ultraviolet Rays
chemical_list: D008670:Metals; D010648:Phenylacetates