Masayuki Moriwaki

An effective chlorinating agent benzyltrimethylammonium tetrachloroiodate, benzylic chlorination of alkylaromatic compounds☆

Abstract The reaction of alkylaromatic compounds with benzyltrimethylammonium tetrachloroiodate in carbon tetrachloride in the presence of AIBN under reflux for several hours gave α-chloro-substituted compounds in fairly good yields.

Halogenation using quaternary ammonium polyhalides. Part 22. Selective bromination of aromatic ethers with benzyltrimethylammonium tribromide

The reaction of aromatic ethers with a stoicheiometric amount of benzyltrimethylammonium tribromide in dichloromethane–methanol or acetic acid–ZnCl2 under mild conditions gave, selectively, mono-, di-, or tri-bromo-substituted aromatic ethers in quantitative yields.

Reactivities of N-(4-Substituted Phenyl)-α-Chloromaleimide in Radical Copolymerization with Styrene or Methyl Methacrylate

Abstract Radical copolymerizations of N-(4-substituted phenyl)-α-chloromaleimide (RPhClMI: 1, R = H; 2, R = Cl; 3, R = OCH3; 4, R = CH3; 5, R = COOC2H5) (M1) with styrene (ST) (M2) or methyl methacrylate (MMA) (M2) in tetra-hydrofuran at 60°C were performed with azobisisobutyronitrile as initiator. This report explores the polymerization behavior of RPhClMI and the substituent effects in copolymerizations. The following reactivity ratios were determined: r 1 = 0.008–0.02, r 2 = 0.056–0.11 in the RPhClMI-ST system and r 1 = 0.021-0.11, r 2 = 0.55–0.63 in the RPhClMI-MMA system. It was found that the relative reactivities (1/r 2) of RPhClMI toward a polystyryl radical was not correlated to the resonance-substituent constant (ER ), but it was correlated to the polar-substituent constant ([sgrave]) in the modified Hammett equation (log (1/r 2) = ρσ + γER ). The M n in the RPhClMI-ST copolymer was 6 000 to 49 000; that of the RPhClMI-MMA copolymer was 2 100 to 9700.