N REACTIVITY VS O REACTIVITY IN AQUEOUS CHLORINATION

Nitrogenated compounds react with hypochlorous acid yielding N-chloro compounds. In principle, alpha-amino acids chlorination may take place on the oxygen of the carboxylic group or on the nitrogen of the amino group. In this framework, we discuss the different reactivities of ni trogen and oxygen towards chlorine, and come to the conclusion that th e nitrogen is the preferred reaction site in alpha-amino acids chlorin ation. (C) 1994 John Wiley & Sons, Inc.