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N,N′‐Diarylurea and Amines from Aroylhydroxamic Acids and β‐Propiolactone. Mechanism of a Double Lossen Reaction
Author(s) -
Knobler Y.,
Frydman N.,
Eliasoff Hanna
Publication year - 1971
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.197100026
Subject(s) - chemistry , nitro , medicinal chemistry , sequence (biology) , stereochemistry , organic chemistry , biochemistry , alkyl
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.