The Reaction of Enamines with N-Dialkylchloramines

The reaction of dialkylchloramines with N-dialkyl-substituted aminoisobutenes was shown to give a mixture of the two α-dialkylaminoaldehydes, which were derived not only from the addition of chloramine, but also from the rearrangement of amino group in the parent enamines. The results suggested an ionic path involving a. cyclic dialkylaziridinium ion as intermediate. The possible mechanism of these reactions was discussed.