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Selected Publication:

A. Patel; T. Netscher; T. Rosenau.
(2008): Stabilization of ortho-quinone methides by a bis(sulfonium ylide) derived from 2,5-dihydroxy-[1,4]benzoquinone
TETRAHEDRON LETT, 49, 2442-2445; ISSN 0040-4039 FullText FullText_BOKU

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 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.
Authors BOKU Wien:
Patel Anjan
Rosenau Thomas
BOKU Gendermonitor:


Find related publications in this database (Keywords)
ortho-Quinone methides
ortho-alkylphenols
aromaticity
sulfonium ylides
zwitterions


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