Catalysis of the aromatic nucleophilic substitution reactions of anilines in aprotic solvents
- 1 January 1988
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 10,p. 1859-1861
- https://doi.org/10.1039/p29880001859
Abstract
The reaction of 1-chloro-2,4-dinitrobenzene with p-anisidine in benzene is catalysed by the nucleophile and by tetra-n-butylammonium chloride. When the nucleophile is N-methyl-p-anisidine the reaction is not catalysed by the nucleophile, tetra-n-butylammonium chloride, DABCO, or pyridine. The reactions of both p-anisidine and N-methyl-p-anisidine with 1-fluoro-2,4-dinitrobenzene have been shown to be catalysed by the nucleophile, tetra-n-butylammonium chloride, and (in the case of N-methyl-p-anisidine) by DABCO and pyridine. Mechanisms are proposed to rationalize the results.Keywords
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