Journal
TETRAHEDRON LETTERS
Volume 49, Issue 15, Pages 2442-2445Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2008.02.045
Keywords
ortho-Quinone methides; ortho-alkylphenols; aromaticity; sulfonium ylides; zwitterions
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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 alpha-tocopherol model compound PMC (5) was comprehensively characterized. As exemplarily demonstrated, the adducts can be advantageously employed in organic synthesis as `stabilized oQMs'. (C) 2008 Elsevier Ltd. All rights reserved.
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