Synthesis and oxidation of ‘non-annulated’ vitamin E-like compounds |
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| Authors: | Thomas Rosenau Amnon Stanger |
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| Institution: | a Department of Chemistry, University of Natural Resources and Applied Life Sciences, Vienna (BOKU), Muthgasse 18, A-1190 Vienna, Austria
b Department of Chemistry, Technion—Israel Institute of Technology, The Institute of Catalysis Science and Technology and The Lise-Meitner-Minerva Center for Computational Quantum Chemistry, Haifa 32000, Israel |
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| Abstract: | Two model compounds (3 and 4) having the typical α-tocopherol-type substitution pattern of the aromatic ring, but lacking the annulated pyran ring, have been synthesized. Upon oxidation, the two possible ortho-quinone methides (oQMs) of each are formed in equal ratio. DFT calculations suggest that there is no angular strain in 3 and 4, and each of the oQM pairs is of similar energy. These results prove that the commonly observed regioselectivity in oxidations of vitamin E-type model compounds is not an electronic substitution effect, but a consequence of annulation. |
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| Keywords: | Tocopherol Vitamin E Antioxidants Mills-Nixon effect Strain-induced bond localization SIBL |
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