The Journal of Organic Chemistry

Carbon-hydrogen vs. carbon-carbon bond cleavage of 1, 2-diarylethane radical cations in acetonitrile-water

DM Camaioni, JA Franz

Index: Camaioni, Donald M.; Franz, James A. Journal of Organic Chemistry, 1984 , vol. 49, # 9 p. 1607 - 1613

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Citation Number: 50

Abstract

R-+ Cu (I1)-+ RCu (II1)-ROH+ CU (I)+ H+(8) of the radical cations, are oxidized to hydroxylic products by Cu2+ ions,* J5 and Cu+ ions, so formed, propagate the oxidation by regenerating SO4-., eq 7. As depicted in Scheme I, alkyl-substituted radical cations undergo competing reactions of side chain fragmentation and hydration. Though hydration is rapid, side chain fragmentation is favored in acidic media because dehydration of the hydroxyl ...

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