Journal of the Chemical Society. Perkin transactions II p. 105 - 108 (1983)
Update date:2022-09-26
Topics:
Cummings, Robert J.
Grundon, Michael F.
Knipe, Anthony C.
Wasfi, Adil S.
Base-catalysed rearrangement of a 2-(hydroxyamino)aryl phenyl sulphone (1b) to the 2-hydroxy-2'-(phenylsulphonyl)azoxybenzene (4b) was shown by isolation and kinetic studies to be a rapid reaction requiring oxygen; in the absence of oxygen the sulphur-free azoxybenzene (3; R=Cl) was the only product isolated from the reaction of (1c).A mechanism for the formation of 2-hydroxyazoxybenzenes (4) is proposed (Scheme 2) involving dimerization of a nitrosoaryl radical anion (9) to the dianion of an NN-diol (10), and displacement of a phenylsulphonyl group by intramolecular transfer of oxygen from a nitrogen atom.A similar study of the base-catalysed reactions of a 2-(hydroxyamino)aryl phenyl sulphide (12) in the presence of oxygen showed that with a poorer leaving group the bis(phenylthio)azoxybenzene (11; R=SPh) is formed.An improved procedure for the preparation of N-arylhydroxylamines from nitrobenzenes is described.
View MoreXinji City Taida Sinopec Co., Ltd.
Contact:0086-311-85341278
Address:No.6, Nanhua Road,Xinji City Road,Hebei Province,China
Guangzhou Probig Fine Chemical Co., Ltd.
Contact:020-86297874
Address:No.2, 1/F, No.20, Hetai Road,Hebian Village, Baiyun District,Guangzhou,China
website:http://www.gbxfsilicones.com/
Contact:86-25-68900673
Address:He Country Provincial Fine Chemical Industrial Park of Chaohu city,Anhui province,China
Contact:+86 021-51698675
Address:1701, Jielong Plaza, No.618 Pingliang Rd, ShangHai,China
Liaoyang Xinyou Chemical Products Co.,Ltd.
Contact:+86-419-5165433 13604191870
Address:Huishang Road6-1, Hongwei District, Liaoyang, Liaoning, China
Doi:10.1246/bcsj.44.541
(1971)Doi:10.1021/ol0260977
(2002)Doi:10.1021/ja411379e
(2014)Doi:10.1021/jo01204a005
(1941)Doi:10.1016/j.jfluchem.2019.109435
(2020)Doi:10.1002/jlcr.3207
(2014)
