Protium–deuterium exchange of benzo-substituted heterocycles in neutral D2O at elevated temperatures Academic Article uri icon

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abstract

  • H–D exchange of 2-methylbenzofuran (1), 2-methylindole (2), 2-methylbenzimidazole (3), 2-methylbenzothiazole (4), and 2-methylbenzoxazole (5) has been studied in neutral D2O at elevated temperatures. While 1, 2, 3, and 4 can be specifically labelled and 4 can be perlabelled at 255 °C, 5 undergoes facile hydrolysis in D2O at 115 °C to 2-acetamidophenol (8) with the incorporation of deuterium into the methyl group. Keywords: H–D exchange, heterocycles, D2O, elevated temperatures.

publication date

  • May 1, 1989