REACTIVITY OF THE ACIDS OF TRIVALENT PHOSPHORUS AND THEIR DERIVATIVES. PART VI. THE REACTION OF THE >P—O⁻ ANIONS WITH BENZYL BROMIDES para-SUBSTITUTED IN THE PHENYL RING

Abstract

The reaction of p-substituted benzyl bromides with the >P—O⁻ ions in THF, alcohols and toluene as the solvents is described. According to the reduction potential of the p-substituted benzyl bromides and the solvent used the formation of the P—C bond, debromination and/or dimerization occur. The principal process is believed to be X-philic substitution, the dimers are formed through a secondary process via SET from the p-substituted benzyl anions into the p-substituted benzyl bromides.

Key Words:

• Michaelis-Becker reaction
• dialkyl phosphites
• dialkylphosphinoxides
• p-substituted benzyl bromides
• p,p'-substituted bibenzyls
• X-philic substitution
• SET