Oxidation of oxazolines and thiazolines to oxazoles and thiazoles. Application of the Kharasch-Sosnovsky reaction
Oxidation of oxazolines and thiazolines to oxazoles and thiazoles. Application of the Kharasch-Sosnovsky reaction
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DOI：
10.1021/jo9613491
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发表时间：
1996-11-15
影响因子：
3.6
通讯作者：
Tavares, FX
中科院分区：
文献类型：
--
作者：
Meyers, AI;Tavares, FX
利用改进的Kharasch-Sosnovsky反应，将带有各种2-烷基取代基（手性和非手性）的恶唑啉和噻唑啉分别顺利地氧化成其相应的恶唑和噻唑。成功实现这一重要氧化的关键特征是使用Cu（I）和Cu（II）盐的混合物来增强中间体捕获自由基的氧化，24。当恶唑啉/噻唑啉在C-4位缺少烷氧羰基时，该方法的主要局限性显示出来。
Using a modification of the Kharasch-Sosnovsky reaction, the oxidation of oxazolines and thiazolines bearing a variety of 2-alkyl substituents (chiral and achiral) were smoothly oxidized to their corresponding oxazoles and thiazoles, respectively. The key feature involved in the successful implementation of this important oxidation was the use of a mixture of Cu(I) and Cu(II) salts to enhance the oxidation of the intermediate captodative radical, 24. The main limitation of this method was shown when the oxidation failed with oxazolines/thiazolines lacking the carboalkoxy group at C-4.