Various N,N-dimethyl aromatic amides were obtained in good to moderate yields by the reaction of aromatic aldehydes with aqueous dimethylamine in the presence of molecular iodine or 1,3-diiodo-5,5-dimethylhydantoin (DIH) at room temperature. Under the same conditions and using the same procedure, treatment of aromatic aldehydes and morpholine in the presence of DIH also provided the corresponding N-aroyl morpholines in good to moderate yields.

AbstractA variety of amines is tested but only dimethylamine and morpholine give amides in moderate to good yields.

AbstractThe introduction of an acetoxy or benzoyloxy group to the benzylic position of alkylbenzenes is achieved using hypervalent iodine compounds (II) in the presence of iodine and sulfonamides.

Treatment of alkylbenzenes with (diacetoxyiodo)benzene in the presence of catalytic amounts of p-toluenesulfonamide or p-nitrobenzenesulfonamide, and molecular iodine in 1,2-dichloroethane at 60 °C gave the corresponding (α-acetoxy)alkylbenzenes in good to moderate yields. The present reaction is a simple method for the introduction of an acetoxy group to the benzylic position of alkylbenzenes.

Treatment of alkylbenzenes with p-toluenesulfonamide and 1,3-diiodo-5,5-dimethylhydantoin (DIH) in a small amount of carbon tetrachloride at 60°C gave the corresponding α-p-toluenesulfonylamido)alkylbenzenes in good to moderate yields. The present reaction is a simple method for the α-sulfonylamidation of the benzylic position in alkylbenzenes.

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