MEISENHEIMER-TYPE COMPOUNDS FROM HETEROAROMATIC SUBSTRATES . REACTION OF METHOXIDE ION WITH 3,5-DINITRO-4-METHOXYPYRIDINE IN METHANOL SOLUTION

The formation and isolation of sodium 4-aza-1,1-dimethoxy-2,6-dinitrocyclohexadienate (adduct III) as resulting from the action of CH3ONa on 3,5-dinitro-4-methoxypyridine in methanol solution are described. The structure of the adduct was proved by spectral evidence (nmr, uv and visible, and ir). The equilibrium constant and the rate of formation have been determined and compared with similar data for the trinitro analog I. The implications of the present results on the influence of aza activation on the mechanism of nucleophilic aromatic substitution are discussed. © 1969, American Chemical Society. All rights reserved.