21623-85-8Relevant academic research and scientific papers
SNAr, SN2, and Aromatic Addition Processes in the Reactions of Picryl Ethers with Nitrogen and Carbon Bases
Strauss, Michael,Torres, Ruben
, p. 756 - 760 (1989)
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 SN2 attack on the methyl group.With more hindered picryl ethers, addition to the ring is more common, resulting in covalent ? complexes, substituted picramides, or bicyclo nitropropenenitronates.In this paper, structural features that influence reaction path are discussed.
