Photostimulated reactions of phenylacetic acid dianions with aryl halides. Influence of the metallic cation on the regiochemistry of arylation.
[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.
Nwokogu
G C
GC
Hampton University, Department of Chemistry, VA 23668, USA.
Wong
J W
JW
Greenwood
T D
TD
Wolfe
J F
JF
D003500:Cyclization; D009682:Magnetic Resonance Spectroscopy; D008670:Metals / Q000737:chemistry*; D010648:Phenylacetates / Q000737:chemistry* / Q000528:radiation effects; D010777:Photochemistry; D014466:Ultraviolet Rays
D008670:Metals; D010648:Phenylacetates