The Interaction of Electrochemically Produced Radical Cations with Substituted Styrenes

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Abstract
Relatively stable radical cations of 9,10-diphenylanthracene (DPA) were formed by controlled potential electrolysis of solutions in acetonitrile. The rates of decay of the ions were measured in the absence and presence of substituted styrenes, including α-methylstyrene, trans-β-methylstyrene, p-methylstyrene, and styrene. In rigorously dried solvent the radical cation was relatively stable, and its rate of decay was independent of its initial concentration. In the presence of monomers the rates of decay were increased greatly and were related to the position of the methyl substituent in the styrene structure.The rate was proportional to [Formula: see text] A mechanism is suggested and interpreted to show that the rates of cation decay are indicative of the rates of propagation in the polymerization process.

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