Abstract
Upon oxidation in aprotic media, β-tocopherol ( 2) forms a spiro-dimer ( 10) as the main product. The reaction mechanism is a hetero-Diels–Alder process with inverse electron demand of two intermediate ortho-quinone methide molecules. The spiro-dimer can be reduced to the corresponding symmetric ethano-dimer ( 11). In contrast to the well-studied α-tocopherol case, spiro-dimer and ethano-dimer do not form a reversible redox pair, their interconversion is accompanied by coupling reactions at C-7 with 7a-(β-tocopher-5a-yl)-β-tocopherol ( 13) as the main byproduct besides some oligomeric material. The full NMR assignments ( 1H, 13C) of the β-tocopherol oxidation products are given.
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