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• W2089303341 abstract "A product and time-resolved kinetic study on the reactivity of the radical cations generated from cyclopropyl(4-methoxyphenyl)phenylmethanol (1) and cyclopropyl[bis(4-methoxyphenyl)]methanol (2) has been carried out in aqueous solution. In acidic solution, 1*+ and 2*+ display very low reactivities toward fragmentation, consistent with the presence of groups at Calpha (aryl and cyclopropyl) that after Calpha-Cbeta bond cleavage would produce relatively unstable carbon-centered radicals. In basic solution, 1*+ and 2*+ display oxygen acidity, undergoing -OH-induced deprotonation from the alpha-OH group, leading to the corresponding 1,1-diarylalkoxyl radicals 1r* and 2r*, respectively, as directly observed by time-resolved spectroscopy. The product distributions observed in the reactions of 1*+ and 2*+ under these conditions (cyclopropyl phenyl ketone, cyclopropyl(4-methoxyphenyl) ketone, and 4-methoxybenzophenone from 1*+; cyclopropyl(4-methoxyphenyl) ketone and 4,4'-dimethoxybenzophenone from 2*+) have been rationalized in terms of a water-induced competition between O-neophyl shift and C-cyclopropyl beta-scission in the intermediate 1,1-diarylalkoxyl radicals 1r* and 2r*." @default.
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• W2089303341 date "2006-03-14" @default.
• W2089303341 modified "2023-10-16" @default.
• W2089303341 title "Oxygen Acidity of Ring Methoxylated 1,1-Diarylalkanol Radical Cations Bearing α-Cyclopropyl Groups. The Competition betweenO-Neophyl Shift and C−Cyclopropyl β-Scission in the Intermediate 1,1-Diarylalkoxyl Radicals" @default.
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• W2089303341 doi "https://doi.org/10.1021/jo0600860" @default.
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