Abstract
Second order rate constants for the 1,3-cycloaddition of diazomethane to benzalanilines (Schiff bases) have been determined. The results do not reveal any general dependence of rate on the dielectric constant of the solvents; there is, however, a definite acceleration in the presence of associated solvents such as water. The kinetic data are discussed and a concerted mechanism postulated for the addition reaction. The significant effect of water on the reaction rate has led to a versatile method for the synthesis of 1,5-diaryl-1,2,3-triazolines in good yields, by the cycloaddition of diazomethane to Schiff bases in aqueous dioxane solutions. Earlier attempts by other workers to react diazomethane with Schiff bases in dry ethereal solutions or in the presence of methanol as catalyst has been largely unsuccessful or has yielded only insignificant amounts of the adduct. At the present time, the cyclo-addition in aqueous dioxane solutions appears to be the only general method of synthesis for the 1,5-diaryl-1,2,3-triazolines.
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