The formation and thermal decomposition of 4-hydroperoxy-2-hydroxy-3,4,6-triisopropylcyclohexa-2,5-dienone |
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Authors: | Abakumov G A Vavilina N N Kurskii Yu A Nevodchikov V I Cherkasov V K Shavyr A S |
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Institution: | (1) G. A. Razuvaev Institute of Organometallic Chemistry, Russian Academy of Sciences, 49, ul. Tropinina, 603600 Nizhnii Novgorod, Russian Federation |
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Abstract: | Auto-oxidation of 3,4,6-triisopropylcatechol affords crystalline 2-hydroxy-4-hydroperoxy-3,4,6-triisopropylcyclohexa-2,5-dienone. Thermal decomposition of the resulting hydroperoxide was carried out and the reaction products were determined. The decomposition mainly proceeds by a route without cleavage of the O—O bond, unusual for hydroperoxides, to give the starting 3,4,6-triisopropylcatechol and 3,4,6-triisopropylbenzo-1,2-quinone. The hydroperoxide decomposes in part according to the traditional pattern involving the O—O bond cleavage to give 3-hydroxy-2,5-diisopropylbenzo-1,4-quinone. |
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Keywords: | quinones catechols oxidation hydroperoxide hydroperoxycyclohexadienone thermal decomposition NMR 2D NMR procedures |
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