Something interesting about (S)-4-Phenylthiazolidine-2-thione

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Research speed reading in 2021. Electric Literature of 185137-29-5, Catalysts allow a reaction to proceed via a pathway that has a lower activation energy than the uncatalyzed reaction. In a document type is Article, and a compound is mentioned, 185137-29-5, (S)-4-Phenylthiazolidine-2-thione, introducing its new discovery.

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.

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Reference:
Quinuclidine – Wikipedia,
Quinuclidine | C7H771N | ChemSpider