Reactivity of aromatic compounds toward diphenylcarbonyl oxide

The reactivity of organic compounds (PhH, PhMe, PhF, PhCl, PhOH, PhOEt, PhC HO, Ph2CO, PhCN, Ph2S, Ph2SO, Ph2SO2, and p-Me2C6H4) toward diphenylcarbony l oxide Ph2COO was characterized by the k(33)/k(31) ratio, where k(33) and k(31) are the rate constants for the reactions of Ph2COO with the arene and diphenyldiazomethane Ph2CN2, respectively. The values of k(33)/k(31) vary from 2.6.10(-3) (PhCN) to 0.65 (Ph2S) (70 degrees C, MeCN). The reaction is preceded by formation of a complex with charge transfer from a substrate t o Ph2COO. In the reactions with aromatic substances (except for Ph2SO, PhCH O, and Ph2CO), carbonyl oxide behaves as an electrophile.