Abstract
The reactivity of organic compounds (PhH, PhMe, PhF, PhCl, PhOH, PhOEt, PhCHO, Ph2CO, PhCN, Ph2S, Ph2SO, Ph2SO2, andp-Me2C6H4) toward diphenylcarbonyl oxide Ph2COO was characterized by thek33/k31 ratio, wherek33 andk31 are the rate constants for the reactions of Ph2COO with the arene and diphenyldiazomethane Ph2CN2, respectively. The values ofk33/k31 vary from 2.6·10−3 (PhCN) to 0.65 (Ph2S) (70°C, MeCN). The reaction is preceded by formation of a complex with charge transfer from a substrate to Ph2COO. In the reactions with aromatic substances (except for Ph2SO, PhCHO, and Ph2CO), carbonyl oxide behaves as an electrophile.
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