64050-49-3Relevant academic research and scientific papers
Thorpe-Ingold effect in the reaction of vicinal amino primary alcohol hydrogen sulfates and carbon disulfide
Chen, Ning,Huang, Zhongyan,Zhou, Chan,Xu, Jiaxi
experimental part, p. 7971 - 7976 (2011/11/14)
The Thorpe-Ingold effect is a key factor that affects the ring-closure rates and efficiency, as well as the structure of products in some ring-closure reactions. The reaction of vicinal amino primary alcohol hydrogen sulfates and carbon disulfide in the presence of potassium hydroxide produces the desired 4,4-disubstituted thiazolidine-2-thiones, and their isomers 5,5-disubstituted derivatives companying with their oxygen analogues 4,4-disubstituted oxazolidine-2-thiones. The formation of 5,5-disubstituted thiazolidine-2-thiones was rationalized via 2,2-disubstituted aziridine-1-carbodithioate intermediates, which were generated due to the Thorpe-Ingold effect. 4,4-Disubstituted oxazolidine-2-thiones were generated from carbon disulfide and free amino alcohols yielded via basic hydrolysis of active amino alcohol hydrogen sulfates in the reaction system.
4- AND 5-HYDROXYLAMINOTHIAZOLIDINE-2-THIONES. REACTION WITH 4-NITROBENZALDEHYDE
Orlova, T. I.,Epshtein, S. P.,Tashchi, V. P.,Putsykin, Yu. G.
, p. 433 - 437 (2007/10/02)
Stable nitrones are formed in the condensation of 5-hydroxylaminothiazolidine-2-thiones with 4-nitrobenzaldehyde.At the same time, nitrones obtained from the isomeric 4-hydroxylaminothiazolidine-2-thiones, as well as 4-hydroxylaminoimidazolidin-2-one, can undergo rearrengement to E- or Z-O-substituted 4-nitrobenzaldoximes, depending on the structure and the reaction conditions.
