The reaction of aromatic amines with benzyltrimethylammonium dichloroiodate(1—) in dichloromethane–methanol in the presence of calcium carbonate powder for several hours at room temperature gave selectively iodosubstituted aromatic amines in good yields.
The reaction of phenols with benzyltrimethylammonium dichloroiodate(1–) in dichloromethane-methanol in the presence of CaCO3 or NaHCO3 for several hours at room temperature gave iodophenols in good yields.
Orange crystalline tetrabutylammonium tribromide was prepared using a simple method. The reaction of acetyl derivatives with an equimolar amount of the tribromide in dichloromethane–methanol at room temperature gave bromoacetyl derivatives in fairly good yields.
Pyrido[2,1-a]isoindole cycloadds to olefinic dipolarophiles in a highly exo-selective fashion giving the kinetically controlled cycloadducts which gradually isomerize into the Michael adducts. With acetylenic dipolarophiles, the hydrogen-migrated cycloadducts are the only products. The mechanism of cycloadditions is discussed.
Ring bromination of aromatic compounds using 1,3-dibromo-5,5-dimethylhydantoin in dichloromethane is promoted by the addition of strong acids. Both organic and inorganic acids whose pKa values are lower than -2 showed the promoting effect. This acid-catalyzed bromination is both practical and effective, even for aromatics having electron-withdrawing substituents.
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