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

The reactions of sodium dimethyl and diisopropyl phosphite, as well as dibe nzylphosphinite with 4-nitrobenzyl chloride, 9-chlorofluorene, and diphenyl chloromethane 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 com patible With the proposed mechanism: a >P-O- anion acts toward an arylmethy l 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 i f it is present in a high enough concentration. (C) 1999 John Wiley & Sans, Inc.