Journal of the American Chemical Society

Catalytic epoxidation of hindered olefins with dioxygen. Fast oxygen atom transfer to olefin cation radicals from nitrogen oxides

E Bosch, JK Kochi

Index: Bosch, Eric; Kochi, Jay K. Journal of the American Chemical Society, 1996 , vol. 118, # 6 p. 1319 - 1329

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Citation Number: 35

Abstract

Hindered olefins are efficiently converted to epoxides by dioxygen at 25° C in dichloromethane containing catalytic amounts of nitrogen oxides (NO2, NO+, NO, etc.). Nitrogen dioxide also effects the direct (stoichiometric) epoxidation of the same hindered olefins. Olefin cation radicals are spectrally identified as the first observable intermediate, and separate experiments confirm the facile transfer of an oxygen atom from nitrogen ...

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