Transmission of substituent effects in pyridines. Part II. Alkaline hydrolysis of some 2-substituted methyl pyridinecarboxylates

Abstract

The alkaline hydrolysis of methyl 6-X-picolinates, methyl 6-X-nicotinates, and methyl 2-X-isonicotinates (X = NO₂, Br, H, Me, MeO, or Me₂N) in methanol–water (85% w/w) at 25° is reported. Deviations from expected behaviour were found in each series and, in the first two, these were related to a resonance effect of X. The relevance of this to ‘ortho-effects’ is discussed.