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• W2059313075 abstract "The title reaction was carried out in aqueous acetonitrile (5% and 20% water) and in nitromethane. Provided acid was not added, the product was mostly the epoxide, accompanied by small amounts of the triol that results from acid-catalyzed ring opening of the epoxide. With added acid, only the triol was detected. The kinetic study afforded a striking result: only the diperoxorhenium compound was an epoxidation catalyst; the monoperoxo compound CH(3)Re(O)(2)(eta(2)-O(2)) was inactive; no other substrates, including nonallylic alkenes, show that reactivity difference. This, together with the realization of high diastereoselectivity for 2-cyclohexen-1-ol in chloroform, suggests a particular mode of hydrogen bonding: an O atom of one peroxo group engages in oxygen transfer, in a transition state that is stabilized by hydrogen bonding between the allylic OH group and O atom of the other peroxo group. Calculations supported that conclusion." @default.
• W2059313075 created "2016-06-24" @default.
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• W2059313075 date "1999-02-12" @default.
• W2059313075 modified "2023-10-18" @default.
• W2059313075 title "Kinetics and Mechanism of the Epoxidation of Allylic Alcohols by Hydrogen Peroxide with Methyltrioxorhenium as Catalyst" @default.
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• W2059313075 doi "https://doi.org/10.1021/ic981107e" @default.
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