Journal of Organic Chemistry p. 3633 - 3638 (1993)
Update date:2022-07-29
Topics:
Sakaue, Sigeki
Tsubakino, Takashi
Nishiyama, Yutaka
Ishii, Yasutaka
Various substituted anilines 1 were selectively converted into the corresponsing nitrosobenzenes 2 or nitrobenzenes 3 by oxidation with aqueous hydrogen peroxide catalyzed by heteropolyoxometalates.The oxidation of anilines 1 with 35percent H2O2 catalyzed by peroxotungstophosphate (PCWP) at room temperature in chloroform under two-phase conditions afforded nitrosobenzene 2 with high selectivity.When the same reactions were carried out at higher temperature (e.g., refluxing chloroform), nitrobenzenes 3 were obtained in good yields.The oxidation of aniline (1a) with dilute H2O2 catalyzed by PCWP (2 wtpercent) in an aqueous medium produced azoxybenzene (4a) with high selectivity.Phenylazoxyalkanes 7 were prepared by the first direct cooxidation of 1a in the presence of primary aliphatic amines 6.For example, the oxidation of a 1:2 mixture of 1a and hexylamine (6b) with 35percent H2O2 (6 equiv) in the presence of PCWP produced phenylazoxyhexane (7b) along with a small amount of 4a (8percent).The reaction path for the conversion of anilines to azoxy-, nitroso-, and nitrobenzenes is described.
View MoreZhejiang Kangfeng Chemical Co.,LTD.
Contact:+86-579-86709687
Address:Xueshizhai Industrial Zone, Weishan Town,Dongyang City, Zhejiang Province ,China
Contact:+86-20-32051076
Address:1105,Building A, International Business Incubator,Science City
Dezhou Longteng Chemical Co., Ltd.
website:http://www.sodium-methoxide.cn/
Contact:0086-18866052283
Address:Xinhua Industrial Zone, Dezhou City, Shandong Province, China
Shandong united-rising pharmaceutical cooperation.,ltd.
Contact:008653187965009
Address:171No., Jing5 Road, Shizhong District, Jinan, China
Suzhou Jingye Medicine & Chemical Co., Ltd
website:http://www.jingyechem.cn
Contact:+86-512-66658588
Address:No. 88, Sanlian Street, Jinfeng Road, Suzhou New District, Jiangsu Province, P. R. China
Doi:10.1021/bi00701a009
(1974)Doi:10.1021/jm970744w
(1998)Doi:10.1039/c1cc11428j
(2011)Doi:10.1039/J19660000150
()Doi:10.1246/bcsj.59.439
(1986)Doi:10.1021/ja00957a031
(1966)