6622-14-6Relevant articles and documents
Hydrophobic polymer-supported catalyst for organic reactions in water: Acid-catalyzed hydrolysis of thioesters and transprotection of thiols
Iimura, Shinya,Manabe, Kei,Kobayashi, Shu
, p. 101 - 103 (2007/10/03)
(Matrix presented) A hydrophobic polystyrene-supported sulfonic acid was found to be effective for hydrolysis of thioesters in pure water. It was revealed that the catalyst was much superior to other Bronsted acid catalysts. Transprotection of thiols from thioesters to thioethers has been successfully performed in water using this catalytic system.
Dehydration reactions in water. Bronsted acid-surfactant-combined catalyst for ester, ether, thioether, and dithioacetal formation in water
Manabe, Kei,Iimura, Shinya,Sun, Xiang-Min,Kobayashi, Shu
, p. 11971 - 11978 (2007/10/03)
Dehydration reactions in water have been realized by a surfactant-type catalyst, dodecylbenzenesulfonic acid (DBSA). These reactions include dehydrative esterification, etherification, thioetherification, and dithioacetalization. In these reactions, DBSA and substrates form emulsion droplets whose interior is hydrophobic enough to exclude water molecules generated during the reactions. Detailed studies on the esterification revealed that the yields of esters were affected by temperature, amounts of DBSA used, and the substrates. Esters were obtained in high yields for highly hydrophobic substrates. On the basis of the difference in hydrophobicity of the substrates, unique selective esterification and etherification in water were attained. Furthermore, chemospecific, three-component reactions under DBSA-catalyzed conditions were also found to proceed smoothly. This work not only may lead to environmentally benign systems but also will provide a new aspect of organic chemistry in water.