Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Epoxidation of Olefins by Iodosylbenzene Catalyzed by Non-Porphyrin Metal Complexes

  • Nam Wonwoo (Department of Chemistry, Ewha Womans University) ;
  • Baek Seung Joong (Department of Chemistry, Ewha Womans University) ;
  • Kazuko I. Liao (Department of Chemistry and Biochemistry, University of California) ;
  • Joan Selverstone Valentine (Department of Chemistry and Biochemistry, University of California)
  • Published : 1994.12.20
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Abstract

Epoxidation of olefins has been studied using iodosylbenzene (PhIO) as the terminal oxidant and binuclear and mononuclear complexes of $Mn^{2+}$, $Co^{2+}$, and $Cu^{2+}$ as catalysts. Epoxides were the predominant products with trace amounts of allylic oxidation products, and the metal complexes were found to be effective catalysts in the epoxidation reactions. The reactivity of binuclear copper complexes was greater than that of the mononuclear copper complexes, whereas the binuclear and mononuclear complexes of $Mn^{2+}$ and $Co^{2+}$ showed similar reactivities. The nature of the ligands bound to copper did not influence the reactivity of the binuclear copper complexes so long as copper ions were held in close proximity. A metal-iodosylbenzene complex, such as suggested previously for Lewis acidic metal complex-catalyzed epoxidation by iodosylbenzene, is proposed as the active epoxidizing species. Some mechanistic aspects are discussed as well.

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