- Reaction of 2,2,5,7,8-pentamethyl-6-chromanol, an α-tocopherol analogue, with NO in the presence of oxygen
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An α-tocopherol model compound, 2,2,5,7,8-pentamethyl-6-chromanol, reacted with nitric oxide (NO) in the presence of various amounts of oxygen to afford four major products. Distribution of the products was varied depending on the ratio of NO and O2
- Nagata, Yoshiko,Nishio, Tamamo,Matsumoto, Shigenobu,Kanazawa, Hideko,Mochizuki, Masataka,Matsushima, Yoshikazu
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p. 2709 - 2712
(2007/10/03)
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- Oxidations of Vitamin E (α-Tocopherol) and Its Model Compound 2,2,5,7,8-Pentamethyl-6-hydroxychroman. A New Dimer
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Oxidation of α-tocopherol (1a) with tert-butyl hydroperoxide in reagent-grade chloroform gave a new dimeric product which appeared to be both aromatic quinonoid.Repetition of the reaction with the tocopherol model compound 2,2,5,7,8-pentamethyl-6-hydroxychroman (1b) gave the corresponding dimer in high yield (30percent).This product was shown by two-dimensional, long-range proton-carbon correlation NMR spectra and subsequently by X-ray diffraction to be 2,3-dihydro-3,3,5,6,9,10,11a(R)-heptamethyl-7a(S)-(3-hydroxy-3-methylbutyl)-1H-pyranoxanthene-8(7aH),11(11aH)-dione (16b).It appeared to be formed by Diels-Alder addition of the intermediate quinone methide 7b to 2-(3-hydroxy-3-methylbutyl)-3,5,6-trimethylbenzo-1,4-quinone (14b), a known product of oxidation.
- Suarna, Cacang,Craig, Donald C.,Cross, Keith J.,Southwell-Keely, Peter T.
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p. 1281 - 1284
(2007/10/02)
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