Canadian Journal of Chemistry p. 1136 - 1146 (1993)
Update date:2022-08-16
Topics:
Martre, Anne-Marie
Danciu, Virginia
Mousset, Guy
The electrochemical behavior of titanium oxysulfate, used as a redox mediator in the reduction of 4, 4'-dinitrodiben-zyl, is studied in a 5 N H 2S04/EtOH 50: 50 medium. The role played by electrogenerated Ti3+ ions in the chemical reduction of nitro groups is also defined. The results obtained allow the determination of the most suitable conditions leading to selective syntheses. Macroscale electrolyses at a constant potential in the presence of TiOS04 give 4, 4'-diaminodi-benzyl with a great purity and a higher yield (93%) than without mediator (75%). The homogeneous chemical reduction of 4, 4'-dinitrodibenzyl by first electrogenerating the Ti3+ ions, then adding the organic substrate, is particularly selective. The nature of the reduction products depends on the [Ti3+]/[dinitro derivative] ratio. The 4-amino-4'-nitrodiben-zyl is synthesized in a 70% yield for a 6: 1 ratio whereas the amount of diamino derivative increases and can constitute the sole reduction product for higher ratios. A comparison is made with 1, 5-and 1, 8-dinitronaphthalenes and 2, 2'-di-nitrodiphenyl. Using a 6: 1 ratio, l-amino-8-nitronaphthalene is not obtained while 45% of l-amino-5- nitronaphthalene and 25% of 2-amino-2'-nitrodiphenyl are formed by reduction of the corresponding dinitro derivatives.
QINGDAO ON-BILLION INDUSTRAIL CO.,LTD
website:http://www.obn.com.cn
Contact:+86-15005320811 +86-532-80681989
Address:F35 Parkson Mansion No.44-60 Zhongshan Rd.
Hangzhou TJM Chemical Trade Co., Ltd
Contact:86-571-88223276 86-13388481653
Address:2221#,Boyuexuan,1860# Binsheng Road,Binjiang District, Hangzhou CityZhejiang Province, 310051, P. R. China
Anhui New Star Pharmaceutical Development Co., Ltd
Contact:013956922763
Address:Floor 3, F9A, F Workshop, No.110 Kexue Road, High-Tech Development Zone, Hefei, Anhui ,China
Nanjing Legend Pharmaceutical & Chemical Co., Ltd.
Contact:+86-25-83767696
Address:14-7 Zhongshan Lu Guluo District, Nanjing
website:http://www.uvchemkeys.com
Contact:0086-021-58785816
Address:RM2607 Building No.1 Guosheng, Lane 388, Zhongjiang Road, Putuo District, Shanghai 200062 China
Doi:10.1021/j100448a002
(1980)Doi:10.1021/jm980323u
(1998)Doi:10.1021/jo00014a030
(1991)Doi:10.1007/s11172-019-2705-y
(2019)Doi:10.1016/S0022-328X(00)99779-1
(1987)Doi:10.1080/00397919308011271
(1993)
