Tetrahedron

Selectivity and mechanism in the side-chain halogenation of methylbenzenes promoted photochemically and by metal complexes in the presence of halide ions

E Baciocchi, M Crescenzi

Index: Baciocchi, Enrico; Crescenzi, Manuela Tetrahedron, 1988 , vol. 44, # 20 p. 6525 - 6536

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Citation Number: 17

Abstract

The intramolecular selectivity in a variety of side-chain halogenations of alkyl-aromatics has been determined in AcOH by measuring the isomeric distribution in the reactions of 4-t-butyl- and 4-chloro-1, 2-dimethylbenzene (1 and 2, respec tively) with: Br2/hν, CAN/Br-, CAN= cerium (IV) ammonium nitrate, cobalt (III) acetate/Br-, S2O8-/Br-, N-bromosuccinimide (in CCl4), Cl2/hν, CAN/Cl-, cobalt (III) acetate/Cl-. In the bromination reactions selectivity is ...