Reaction of Aromatic and Unsaturated Compounds with the Potassium Permanganate/HCI (HBr) Acetonitrile Reagent

Article abstract of DOI:10.1002/jccs.199600010

Addition of hydrochloric or hydrobromic acid to a solution of potassium permanganate in acetonitrile produced a homogeneous mixture, which is suitable for laboratory chlorination or bromination, respectively. Aromatic compounds more reactive than alkylbenzenes can be chlorinated or brominated without additional catalyst. Alkenes and alkynes give the corresponding vicinal dihaloalkanes and vinyl halides. All reactions complete within two hours under mild condition (25-60 °C) with excellent to moderate yields.