The reactions of methyl, cyclohexyl, and phenyl picryl ethers with diethyl-and triethylamine in chloroform, acetone, and 1, 3-dicarbomethoxyacetone have been studied. A number of different processes were observed, depending on substrate structure. Both amine nitrogen and enolate carbon act as nucleophiles in these reactions. With unhindered picryl ethers like 2, 4, 6-trinitroanisole, dealkylation often occurs via SN~ attack on the methyl group. With ...
