1984 Volume 57 Issue 6 Pages 1586-1590
Condensation of 1,4-cyclohexanedione with N-alkylarylamines gives N-alkyl-N-arylanilines, and that with diarylamines gives triarylamines. A mechanism involving dehydration of monoenamines of the 1,4-dione is proposed for the reaction. Relative rates of substituted N-ethylanilines on competitive reactions plotted vs. Hammet’s σ values gave −2.0 as the ρ value. In separate reactions, however, a different tendency is noted for the yield, that is, the ease of reactions with p-chloro and p-nitro derivatives. This discrepancy is explained in terms of acidities of the conjugate acids of the amines used as the actual catalysts.
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