1,2-Dimethoxybenzene and 3,4-dimethoxytoluene are efficiently chlorinated by N-chlorodialkylamines in sulphuric acid. The reaction has a very marked selectivity for monochlorination of the para-position. The chlorination and bromination of monoalkylbenzenes (toluene, ethyl-, and isopropylbenzenes) under the same conditions is much less selective, but the para/ortho ratio can be reversed going from unsubstituted alkyl groups in the N-halogeno amines to alkyl groups substituted at the β-position by electron-withdrawing groups [morpholine, piperazine, bis(cyanoethyl)amine]. m-Xylene is chlorinated with high selectivity at the 4-position. The nature of the chlorinating species is discussed.

(1989). Selective aromatic chlorination and bromination with N-halogeno amines in acidic solution [journal article - articolo]. In JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS II. Retrieved from https://hdl.handle.net/10446/231776

Selective aromatic chlorination and bromination with N-halogeno amines in acidic solution

Fontana, Francesca;
1989-01-01

Abstract

1,2-Dimethoxybenzene and 3,4-dimethoxytoluene are efficiently chlorinated by N-chlorodialkylamines in sulphuric acid. The reaction has a very marked selectivity for monochlorination of the para-position. The chlorination and bromination of monoalkylbenzenes (toluene, ethyl-, and isopropylbenzenes) under the same conditions is much less selective, but the para/ortho ratio can be reversed going from unsubstituted alkyl groups in the N-halogeno amines to alkyl groups substituted at the β-position by electron-withdrawing groups [morpholine, piperazine, bis(cyanoethyl)amine]. m-Xylene is chlorinated with high selectivity at the 4-position. The nature of the chlorinating species is discussed.
articolo
Minisci, Francesco; Vismara, Elena; Fontana, Francesca; Platone, Eduardo; Faraci, Giovanni
(1989). Selective aromatic chlorination and bromination with N-halogeno amines in acidic solution [journal article - articolo]. In JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS II. Retrieved from https://hdl.handle.net/10446/231776
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10446/231776
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