Fundamental Chemistry of Phenols and Antioxidants

  • Reactivity of tocopherols and related antioxidants
  • Primary oxidation intermediates of alkylphenols
  • ortho-Quinone methide chemistry
  • Spiro-dimerization and apiro-polymerization reactions
  • Design of multi-functional stabilizers for polymers
  • Experimental, theoretical and computational studies of antioxidative action

Key publications:

  1. Rosenau, T.; Potthast, A.; Elder, T.; Lange, T.; Sixta, H.; Kosma, P. J. Org. Chem. 2002, 67 (11), 3607-3614. Synthesis and oxidation behavior of 2,4,5,7,8-pentamethyl-4H-1,3-benzodioxin-6-ol, a multi-functional oxa-tocopherol type antioxidant.
  2. Rosenau, T.; Potthast, A.; Hofinger, A.; Kosma, P. Angew. Chem. Int. Ed. 2002, 41 (7), 1171-1173. Calixarene-type macrocycles by oxidation of phenols related to vitamin E.
  3. Rosenau, T.; Potthast, A.; Elder, T.; Kosma, P. Org. Lett. 2002, 4(24), 4285-4288. Novel Tocopheryl Compounds XIII. Stabilization and first direct spectroscopic evidence of the ortho-quinone methide derived from vitamin E.
  4. Adelwöhrer, C.; Rosenau, T.; Gille, L.; Kosma, P. Tetrahedron 2003, 59(15), 2689-2693. Synthesis of novel 3-oxa-tocopherol type antioxidants.
  5. Rosenau, T.; Ebner, G.; Stanger, A.; Perl, S.; Nuri, L. Chem. Eur. J. 2005, 11(1), 280-287. From a Theoretical Concept to Biochemical Reactions: Strain Induced Bond Localization (SIBL) in Oxidation of Vitamin E.
  6. Gregor, W.; Grabner, G.; Adelwöhrer, C.; Rosenau, T.; Gille, L. J. Org. Chem. 2005, 70(9), 3472-3483. Antioxidant Properties of Natural and Synthetic Chromanol Derivatives: a Study by Fast Kinetics and Electron Spin Resonance Spectroscopy.
  7. Rosenau, T.; Kloser, E.; Gille, L.; Mazzini, F.; Netscher, T. J. Org. Chem. 2007, 72(9), 3268-3281. Studies into the chemistry of initial oxidation intermediates of a-tocopherol: disproving the involvement of 5a-C-centered “chromanol methide” radicals.
  8. Patel, A.; Netscher, T.; Rosenau, T. Tetrahedron Lett. 2008, 49, 2442-2445. Stabilization of ortho-quinone methides by a bis(sulfonium ylide) derived from 2,5-dihydroxy-[1,4]benzoquinone.