Migration of electronegative substituents. I. Relative migratory aptitude and migration tendency of the carbethoxy group in the dienone-phenol rearrangement

JN Marx, JC Argyle, LR Norman

Index: Marx,J.N. et al. Journal of the American Chemical Society, 1974 , vol. 96, p. 2121 - 2129

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Citation Number: 59

Abstract

Abstract: The rearrangement, in trifluoroacetic acid at 38.5 O, of two series of 4, 4- disubstituted cyclohexadienones to give 3, 4-disubstituted phenols has been studied. In the first series, a carbethoxy group is placed in intramolecular migratory competition with other common substituents (Me, Et, Ph, i-Pr, Bz). The carbethoxy group is found to migrate in preference to Me, Et, or Ph with relative rates of 1: 0.45: 135. In the case of the i-Pr and Bz ...