Effect of the Position of Reaction-Site in Amphipathic-Type Thioester in Aqueous Amidation Reaction

• 作者: Chiaki Kuroda Ikumi Otomo
• 来源期刊: 化学工程与科学期刊(英文)
• 学科: 化学
• 关键词: Hydrophobic EFFECT AMIDES THIOESTERS
• 年，卷（期）: 2015,（3）
• 页码范围: 311-316
• 页数: 6页
• 分类号: O6

摘要

Amphipathic-type thioesters CH3(CH2)mCOS(CH2)nCOONa (m + n = 12) were synthesized and their reaction with various alkylamines was examined. Compounds having thioester moiety close to carboxylate (m = 10, n = 2) afforded the corresponding amides in good yields, while the substrate having thioester moiety distant from carboxylate (m = 2, n = 10) afforded the amides in relatively low yield. In all cases, the difference in yield due to the chain length of amine was not observed. The results indicated that the reaction took place effectively near the surface of micelle. However, the reaction was found to occur not only on micelle surface but also in solution.