MONO(m-SUBSTITUTED) CHLOROACETYLDIARYLAMINES IN THE STOLLE REACTION

Article abstract of DOI:10.1007/BF00568949

The effect of substituted (OCH3, Cl) on the ratio of the isomeric N-aryloxindoles formed in the Stolle reaction from mono(m-substituted) chloroacetyldiarylamines was studied.It was shown by means of gas-liquid chromatography (GLC) and PMR spectroscopy that in the case of the methoxy group electrophilic substitution occurs only in the ring activated by the substituent.The presence of a halogen atom leads only to 1-(m-chlorophenyl)oxindole.The results show that high selectivity of the attack by the carbonium ion on the phenyl rings with electron-donor and electron-acceptor substituents is also retained in the case of intramolecular electrophilic substitution under conditions of kinetic control.