The Journal of Organic Chemistry

Selective autoxidation of electron-rich substrates under elevated oxygen pressures

PE Correa, G Hardy, DP Riley

Index: Correa, Paul E.; Hardy, Gordon; Riley, Dennis P. Journal of Organic Chemistry, 1988 , vol. 53, # 8 p. 1695 - 1702

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Citation Number: 43

Abstract

We report here the observation of a novel autoxidation pathway which occurs with electron- rich substrates. Tertiary amines, dialkyl thioethers, olefins, and alkynes under high oxygen pressures (> 20 bars of 02), in polar solvents, and at elevated temperatures (> 90" C) yield in good to excellent selectivity amine oxides, sulfoxides, and site-specific olefin and alkyne cleavage products, respectively. The results of mechanistic studies, including high oxygen ...