Metal ions and complexes in organic reactions. Part XII. Copper-catalysed reaction between 2-bromonitrobenzene and diphenylamine
- 1 January 1970
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society C: Organic
- No. 14,p. 1973-1975
- https://doi.org/10.1039/j39700001973
Abstract
Copper-catalysed nucleophilic substitution of the type NHAr2+ Ar′Br → NAr2Ar′ occurred in dimethylacetamide between diphenylamine and o-bromonitrobenzene, giving NN-diphenyl-o-nitroaniline (ca. 50%), accompanied by nitrobenzene (up to 50%), a compound of probable structure o-NO2·C6H4·NPh·C6H4·NPh2(up to 3%), and only traces of 2,2′-dinitrobiphenyl. Methyl o-bromobenzoate was less reactive, and m- and p-bromonitrobenzene were unreactive. Heterogeneous copper catalysts (preferable Cu2O) were much superior to homogeneous catalysts (CuHal) for this particular nucleophilic substitution.Keywords
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