Chemistry of ethanediyl S,S-acetals 6-an example of vicarious nucleophilic substitution of hydrogen in 1,4-benzodithians

Article abstract of DOI:10.1016/S0040-4020(01)81819-6

1,4-Benzodithians, when treated with bromine in anhydrous chloroform, undergo very fast monobromination at the aromatic ring. By the use of quantum mechanical semiempirical calculations, the reaction is shown to proceed most likely via a vicarious nucleophilic substitution of hydrogen.