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 MoreBeijing Wisdom Chemicals Co., Ltd.
Contact:+86-10-52350335
Address:F2, BLDG 19, Liando Valley U, Majuqiao, Tongzhou District, Beijing, China
Contact:+44 (0)2036089360-31
Address:Chanceryhouse,Chancery Lan
Huangshi Shennong Chemical Technology Co., Ltd
Contact:+86-714-3072290
Address:Eastern industrial park , Tieshan district , Huangshi city ,Hubei province , China
Anhui Redstar Pharmaceutical Corp., Ltd
Contact:+86-563-5120837
Address:Jingxian Industrial Development Zone, Anhui , China
HEZE KINGVOLT CHEMICAL CO., LTD
Contact:86-573-82118911
Address:Juancheng Industry Park
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)
