Reactivity of the <P-O- nucleophiles toward arylmethyl chloride systems

The reactions of sodium dimethyl and diisopropyl phosphite, as well as dibenzylphosphinite with 4-nitrobenzyl chloride, 9-chlorofluorene, and diphenylchloromethane weve studied in detail by the isolation and identification of all the products, and the examination of the effects of title solvents on the product distribution. The results of the performed experiments nl-e compatible With the proposed mechanism: a >P-O- anion acts toward an arylmethyl chloride as a base and abstracts a proton to form a carbanion, which can then participate in the SET processes to produce carbon-centered radicals. Additionally, the >P-O- reagent can act as a carbon-centered radical trap if it is present in a high enough concentration. (C) 1999 John Wiley & Sans, Inc.