Carbonyl oxide chemistry. Part 2. Substituent and solvent effects on the chemical behaviour of carbonyl oxides

Abstract

Comparison of the behaviour in polar and apolar solvents at various concentrations of the monoaryl carbonyl oxides 1 bearing an electron-withdrawing or an electron-donating group, respectively, on the aryl substituent is reported. The results are consistent with the conversion pathways reported in Scheme 1 and show that the electron-donating group increases the intramolecular oxygen-transfer potential of the system. It is also proposed that under some experimental conditions the carbonyl oxides so substituted mainly isomerize into dioxiranes 11.