rates of N-methylation of 2-Methybenzotriazole, 2,1,3-Benzoxadiazole, 2,1,3-Benzothia(or Selena)diazole, 1,2,5-Oxadiazole and 1,2,5-Thiadiazole

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Abstract
The rates of quaternization of the title compounds with dimethyl sulphate are reported. The reactivity order is Se > NMe > S > O; benzofusion has only a small rate-diminishing effect.