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This is consistent with a reaction mechanism involving initial ESIPT from the phenol OH to the 2′-position of the adjacent phenyl ring, to generate a biphenyl quinone methide intermediate which rapidly tautomerizes back to starting material.
The κ-btz complexes 2 a– d appeared to be remarkably stable in solution at room temperature, reverting back to starting material only very slowly when samples are left in the dark.
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Further, these samples were placed in the refrigerator to slow the rate of reversion of the intermediate back to the starting material.
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It was found that BPA undergoes a chemically irreversible voltammetric oxidation process to form compounds that cannot be electrochemically converted back to the starting materials on the voltammetric timescale.
In both solvents, longer timescale (minutes to hours) controlled potential coulometry experiments indicated that the oxidation process occurred by two-electrons per molecule, to form reactive diamagnetic cations that could not be reduced back to the starting materials under electrolysis conditions.
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