Abstract

Abstract The reaction of o-, m- and p-nitrobenzyl bromide with sodium dimethylphosphite as well as sodium diisopropylphosphite in THF and alcohols as the solvents is described. According to the constitution of the starting materials and the solvent used, the formation of the P–C bond, debromination or dimerization occurs. The principal process in o- and p-nitrobenzyl bromide and >P-O− anion systems is believed to be X-philic substitution, the dimer is formed through a secondary process via SET from the nitrobenzyl anion to nitrobenzyl bromide. Electron-transfer and proton-transfer processes in the nitrobenzyl bromide->P–O− systems are also discussed.

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