Anodic oxidation of triphenylphosphinephenylimine

✍ Scribed by Christine J. Woerner; Wilson M. Gulick Jr.

• Publisher: Elsevier Science
• Year: 1977
• Tongue: English
• Weight: 457 KB
• Volume: 22
• Category: Article
• ISSN: 0013-4686
• DOI: 10.1016/0013-4686(77)85099-8

✦ Synopsis

Anodic

oxidation of triphenylphosphinephenylimine in acetonitrile has been examined by voltammetry, controlled potential coulometry, and electron spin resonance spectroscopy. Product analy ses showed that triphenylphosphine oxide and mixtures of polymeric oxidized salts of aniline are major products along with unreactcd starting material. A reaction sequence is proposed in which the primary electrode reaction is a one-electron oxidation followed by rapid cleavage of the radical cation at the P-N bond and reaction of the fragments with solvent. Aniline is oxidized anodically to form various polymeric species and liberate protons. Protonation of the starting material renders it electrochemically inert with the result that a large proportion of it is recovered.