The Journal of Organic Chemistry

SNAr, SN2, and aromatic addition processes in the reactions of picryl ethers with nitrogen and carbon bases

M Strauss, R Torres

Index: Strauss, Michael; Torres, Ruben Journal of Organic Chemistry, 1989 , vol. 54, # 4 p. 756 - 760

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Citation Number: 9

Abstract

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 ...

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