ipso Nitration in p-halophenyl ethers

…, A Fischer, GN Henderson

Index: Clewley, Robin G.; Fischer, Alfred; Henderson, George N. Canadian Journal of Chemistry, 1989 , vol. 67, p. 1472 - 1479

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Citation Number: 16

Abstract

Addition of nitronium ion ipso to halogen occurs on nitration of the p-haloanisoles in acetic anhydride at-60° C. In the cases of p-fluoro-and p-chloro-anisole, addition of the nitronium ion is reversible and only small amounts of ipso products are obtained. With p-bromoanisole nitrodebromination occurs. When p-halophenyl ethers containing a trapping substituent, eg, 2-(4-chlorophenoxy)-2-methylpropanoic acid, are used as substrates, substantial amounts ...