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 thek 33/k 31 ratio, wherek 33 andk 31 are the rate constants for the reactions of Ph2COO with the arene and diphenyldiazomethane Ph2CN2, respectively. The values ofk 33/k 31 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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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2197–2201, November, 1998.
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Nazarov, A.M., Yamilova, G.A., Khursan, S.L. et al. Reactivity of aromatic compounds toward diphenylcarbonyl oxide. Russ Chem Bull 47, 2129–2133 (1998). https://doi.org/10.1007/BF02494266
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DOI: https://doi.org/10.1007/BF02494266