Tetrahedron Letters

Stabilization of ortho-quinone methides by a bis (sulfonium ylide) derived from 2, 5-dihydroxy-[1, 4] benzoquinone

A Patel, T Netscher, T Rosenau

Index: Patel, Anjan; Netscher, Thomas; Rosenau, Thomas Tetrahedron Letters, 2008 , vol. 49, # 15 p. 2442 - 2445

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Citation Number: 13

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) ...