Journal of Organometallic Chemistry p. 401 - 409 (1991)
Update date:2022-08-02
Topics:
Hoberg, Heinz
Baerhausen, Dieter
It is shown that 4-pentencarboxylic acid anilide (I), which can readily be prepared catalytically from ethene and phenyl isocyanate (II), further reacts with II on ligand-nickel(0)-systems in a highly regioselective reaction to form triphenylphosphine-5-azanickelacyclopentan-4-one (Va).Protonolysis of Va leads to adipic acid anilide.When Va is treated with maleic acid anhydride at 20 deg C. a β'-H-elimination, is induced because the hydrolysis gives the symmetric 3-hexendicarboxylic acid dianilide (XII) with high selectivity.The catalytic reaction of I and II on a ligand-nickel(0)-complex (ligand = tricyclohexyl-phosphite) involves a β-H-elimination to yield 2-hexendicarboxylic acid dianilide (XI).This opens up the possibility of producing adipic acid derivatives catalytically in a two step synthesis from ethene and phenyl isocyanate.The mechanisms and special features are discussed.
View MoreSICHUAN ZHONGBANG NEW MATERIAL CO., LTD
website:http://www.zhongbangst.com
Contact:86-830-2585019
Address:sichuan,china
Dalian RSD International Trade Co.,Ltd.(expird)
Contact:86-22-60875058 58610575
Address:Wantong International Areas, Hongqiao District, Tianjin, China.China
Contact:86-311-83160559
Address:shijiazhuang
website:http://www.sagechem.com
Contact:+86-571-86818502
Address:Room C1301, New Youth Plaza, 8 Jia Shan Road, Hangzhou, China
Jiangxi Lanqi Fine Chemical S&T Co., Ltd.
Contact:+86-21-64891143
Address:XinJiShan Industrial Area, Zhangshu City, JiangXi Province, China
Doi:10.1021/acs.joc.0c02024
(2020)Doi:10.1021/ol301730c
(2012)Doi:10.1021/ja953682c
(1996)Doi:10.1016/j.dyepig.2011.05.005
(2012)Doi:10.1055/s-0030-1260070
(2011)Doi:10.1246/cl.2011.834
(2011)