Abstract
The zwitterionic intermediates ( 2a) in the oxidation of ortho-alkylphenols ( 1) and bis(sulfonium ylide) 3 form reasonably stable 2:1-complexes ( 4), in which the ortho-quinone methide ( oQM) moieties are not present in quinoid form with the exocyclic in-plane methylene group, but as zwitterionic, aromatic conformer having an out-of-plane exocyclic methylene group. The complex 7 derived from the α-tocopherol model compound PMC ( 5) was comprehensively characterized. As exemplarily demonstrated, the adducts can be advantageously employed in organic synthesis as ‘stabilized oQMs’.
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