A New View of the Arylhydroxylamine Rearrangement

Abstract

DR. BRAUDE'S published statement on the matter is short enough to be quoted : “It is very probable, however, that the acid-catalysed rearrangement of phenylhydroxylamine, and allied reactions, proceeds by way of successive pentad anionotropic and prototropic changes in the C : C.C : C.N skeleton, as originally suggested by Bamberger. The rearrangement may occur in two steps, the migrating group becoming first attached to the orthocarbon atom.” At a later point he entertains the possibility that the rearrangement is intramolecular. This will make his position clear. We did not refer to it before, because we could accept it only in such a very partial way.