Nucleophilic Substitution with Phosphide Anions Prepared by an Action of Sodium Dihydridobis(2-methoxyethanolato)aluminate on Phosphorus Compounds

Article abstract of DOI:10.1246/bcsj.56.219

Phosphide anions, prepared by an action of sodium dihydridobis(2-methoxyethanolato)aluminate on derivatives of phosphine, phosphine oxide, or phosphorus esters, react with primary and secondary alkyl halides to produce phosphine derivatives having a newly formed phosphorus-carbon bond.The reactivity increases in the order of chloride < bromide < iodide and of secondary < primary in alkyl halide.Reaction of phosphide anion is also feasible with p-toluenesulfonate.Reaction of an anion of diphenylphosphine oxide seems to proceed mainly as an S_N2 type process.