E. Grovenstein, A. M. Bhatti, F. Plagge
Sep 1, 1990
Citations
0
Influential Citations
3
Citations
Journal
Organometallics
Abstract
Both 3,3-diphenyl-1-butene and triphenylmethane react with excess Cs-K-Na alloy in THF at -75°C to give a red dianion of unique structure involving [1,2]-phenyl migration into an adjacent benzene ring, according to structural characterization of the products of protonation and deuteration. The dianion from the butene is assigned the structure dicesium 6-(cis-1'-methyl-2'-propen-1'-id-1'-yl)-6-phenylcyclohexa-2,4-dien-1-ide and that from triphenylmethane dicesium 6-(phenylmethanidyl)-6-phenylcylclohexa-2,4-dien-1-ide. Tetraphenylmethane evidently undergoes a similar reaction with Cs-K-Na alloy, but the product of [1,2]-phenyl migration largely undergoes fragmentation prior to or following protonation. In contrast 1,1,1-triphenylethane reacts with Cs-K-Na alloy at -75°C to give an ortho-cyclized dianion, dicesium 9-methyl-9-phenyl-cis-4a,4b-dihydrofluoren-2,5-diide