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The reaction of alkyl phenyl ethers with sodium chlorite in dichloromethane in the presence of a (salen)manganese(III) complex and alumina preloaded with a small amount of water afforded monochlorination products with unusually high para selectivities under mild conditions. The NaClO2-based biphasic system can also be successfully used for the regioselective monochlorination of substituted anisoles and polymethoxybenzenes. Keywords: aromatic chlorination, alkyl aryl ethers, sodium chlorite, (salen)manganese(III) complex, alumina.

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An inexpensive combination of common laboratory reagents, dimethyl sulfoxide (DMSO) and chromatographic neutral alumina, gives an efficient, selective, and high-yielding oxidation of aromatic, aliphatic and alicyclic thiols to the corresponding disulfides in excellent yields under relatively mild conditions.