Journal of the Chemical Society. Perkin transactions II p. 1473 - 1478 (1988)
Update date:2022-09-26
Topics:
Baltes, Michel
Cazaux, Louis
Gorrichon, Liliane
Maroni, Pierre
Tisnes, Pierre
t-Butyl N-arylsulphinamoylacetates are hydrolysed in aqueous basic media by an elimination mechanism. It takes place on the conjugate base of the substrate resulting from a fast deprotonation of the activated methylene group. This elimination is first order (E1cB) for compounds where strong electron-withdrawing groups substitute the aromatic ring. For substitution by weaker electron-withdrawing or -donating groups, the elimination is second order, and needs the presence of general acid catalysis. For t-butyl N-(2-hydroxyphenyl)sulphinamoylisobutyrate where this mechanism of elimination is impossible, a BAc2 attack by hydroxide ion at the sulphur atom takes place. From these mechanisms and the results of complexation of zinc(II) cations by sulphinamoylacetates, a possible scheme for the irreversible inactivation of the title zinc metalloenzyme is proposed.
View MoreYingkou Sanzheng Organic Chemical Co. Ltd.
Contact:+86-417-3638818
Address:25 Gengxinli Village, Daqing Road, Yingkou, Liaoning, China
Chengda Pharmaceuticals Co., Ltd.
Contact:+86-573-84601188
Address:hengshan Road 5# in Jiashan, zhejiang
Contact:+86-717-6370352
Address:168 Chengdong Avenue, Yichang, Hubei 443003, P. R.China
Changsha Goomoo Chemical Technology Co.Ltd
Contact:+86-731-82197655
Address:No.649,Chezhan Rd.(N),Changsha,Hunan,China
website:http://www.hanwayschem.com
Contact:+86-18502787239(whatsapp)
Address:18-1-802, Green Garden, Jianghan District, Wuhan 430023, China
Doi:10.1021/jm201045m
(2011)Doi:10.1021/ja01528a039
(1959)Doi:10.1016/S0040-4039(00)83940-4
(1986)Doi:10.1016/S0040-4039(00)96818-7
(1987)Doi:10.1039/b906266a
(2009)Doi:10.1016/S0040-4020(01)86649-7
(1988)
