Reactivity of aromatic compounds toward diphenylcarbonyl oxide

Article abstract of DOI:10.1007/BF02494266

The reactivity of organic compounds (PhH, PhMe, PhF, PhCl, PhOH, PhOEt, PhCHO, Ph₂CO, PhCN, Ph₂S, Ph₂SO, Ph₂SO₂, and p-Me₂C₆H₄) toward diphenylcarbonyl oxide Ph₂COO was characterized by the k₃₃/k₃₁ ratio, where k₃₃ and k₃₁ are the rate constants for the reactions of Ph₂COO with the arene and diphenyldiazomethane Ph₂CN₂, respectively. The values of k₃₃/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.