Der Mechanismus der Reaktion von Benzhydroxamsäure (I)‐Na‐Salz mit dem Propiolacton (II), als deren Endprodukt Diphenylharnstoff (V) (93% Ausbeute) entsteht, wird eingehend untersucht.
It has been shown that N,N′‐diphenylurea formation in the reaction of benzohydroxamic acid and β‐propiolactone constitutes a sequence of two rearrangements of the Lossen type. The intermediates, O‐(β‐hydroxypropionyl)benzohydroxamate and O‐(N‐phenylcarbamoyl)benzo‐hydroxamate, have been isolated as products of consecutive steps. Their transformations have been shown independently and along the process leading to N,N′‐diphenylurea. Heating of sodium benzohydroxamate, p‐nitro‐ and p‐methoxy‐benzohydroxamate with β‐propiolactone afforded N, N′‐diphenylurea, p‐nitroaniline and N,N′‐di‐p‐methoxyphenylurea, respectively. Improved procedures for preparation of aroylhydroxamic acids are described.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.