Abstract
The reaction of sodium diisopropyl phosphite with p-nitrobenzyl bromide was studied in detail by (1) isolation and identification of all products and (2) studying the effects of radical traps, such as dicyclohexylphosphine, di-tert-butylnitroxide, and the diisopropyl phosphite anion, on product distribution. The results of the experiments carried out are compatible with a proposed X-philic substitution/SET tandem mechanism. It was demonstrated that p-nitrobenzyl chloride is also a good single-electron acceptor from the p-nitrobenzyl anion. The anion radical derived from p-nitrobenzyl chloride decomposes into the p-nitrobenzyl radical, which couples with an appropriate anion if it is present in a high enough concentration in the reaction mixture, to produce the dimer or the p-nitrobenzylphosphonate. © 1996 John Wiley & Sons, Inc.
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