Reaction of hypohalous acids with 2-halogenopropenes. Exchange of halogen atoms. Part II

Abstract

2-Chloropropene reacts with [³⁶Cl]hypochlorous acid in the presence of excess of silver ion to form chloroacetone (85%) and 2,3-dichloropropene (15%) both with a much reduced specific activity. The radioactivity in the 2,3-dichloropropene was shown to be exclusively in the 3-chloro-substituent. The loss of activity was decreased as the initial silver-ion concentration was increased. Similar exchange occurred in the reaction of 2-bromopropene with [⁸²Br]hypobromous acid and the reaction of hypochlorous acid with 2-bromopropene produced bromoacetone as well as chloroacetone. Addition of halide ion to [³⁶Cl]hypochlorous acid containing excess of silver ion showed the expected variation with silver ion of the radioactivity formed in solution which also decreased in the order Cl^– > Br^– > l^–.