Polyfluoroaryl organometallic compounds. Part XVI. Reactions of organolithium compounds with halogenated benzils
Reactions of alkyl- or aryl-lithiums with decafluorobenzil gave adducts which undergo rapid pentafluorophenyl migration. A variety of products were obtained after hydrolysis, depending on the lithio-derivative used: ketoalcohols, a benzo[b]furan derivative (from C6F5Li), and bis(pentafluorophenyl)methyl pentachlorobenzoate (from C6Cl5Li). The mechanisms of these processes are discussed. Some analogous reactions of benzil are described for comparison and relative migratory aptitudes of groups in these processes are examined.