Journal of Organic Chemistry p. 756 - 760 (1989)
Update date:2022-08-03
Topics:
Strauss, Michael
Torres, Ruben
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 <3.3.1> nitropropenenitronates.In this paper, structural features that influence reaction path are discussed.
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