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Syntheses of Perfluorinated Epoxides, Diepoxides, and a Novel Rearrangement#

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t-Butylhydroperoxide/butyl-lithium is a good reagent for synthesis of epoxides and diepoxides from polyfluorinated -alkenes and -polyenes. This reagent and calcium hypochlorite both give a novel diepoxide 5 from perfluoro-3,4-dimethyl-2,4-diene 1; diepoxide 5 undergoes a novel rearrangement, at 200 °C, to the corresponding 1,4-dioxine derivative 18. Possible mechanisms are discussed.

Affiliations: 1: Department of Chemistry, University Science Laboratories, South Road, Durham DH1 3LE, U.K.


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