Gold-catalyzed aerobic epoxidation of trans-stilbene in methylcyclohexane. Part II: Identification and quantification of a key reaction intermediate
KAUST DepartmentKAUST Catalysis Center (KCC)
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AbstractThe gold-catalyzed aerobic oxidations of alkenes are thought to rely on the in situ synthesis of hydroperoxide species, which have however never been clearly identified. Here, we show direct experimental evidence for the presence of 1-methylcyclohexyl hydroperoxide in the aerobic co-oxidation of stilbene and methylcyclohexane catalyzed by the Au/SiO2-R972 optimized catalyst prepared in Part I. Determination of its response in gas chromatography, by triphenylphosphine titration followed by 31P NMR, allows to easily follow its concentration throughout the co-oxidation process and to clearly highlight the simultaneous existence of the methylcyclohexane autoxidation pathway and the stilbene epoxidation pathway. © 2012 Elsevier B.V. All rights reserved.
SponsorsFunding of K.G. PhD fellowship by the French National Research Agency (ANR-08-JCJC-0090-01-ACTOGREEN project) is gratefully acknowledged. The authors thank Dr V. Mendez (IRCELYON) for fruitful discussions. This publication is based on work partly supported by Collaborative Travel Funds, made by King Abdullah University of Science and Technology (KAUST).
Conference/Event name10th European Workshop Meeting on Selective Oxidation, The Silver Jubilee Meeting" Selectivity: the Key to Sustainability "