Divergent Reactivity in the Reaction of 尾-Oxodithioesters and Hydroxylamine: Access to 尾-Ketonitriles and Isoxazoles

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• 作者：Jiaheng Li ; Wei Ma ; Wenbo Ming ; Cong Xu ; Na Wei ; Mang Wang
• 刊名：Journal of Organic Chemistry
• 出版年：2015
• 出版时间：November 6, 2015
• 年：2015
• 卷：80
• 期：21
• 页码：11138-11142
• 全文大小：402K
• ISSN：1520-6904

文摘

Starting from 尾-oxodithioesters and hydroxylamine, two completely different transformations afford either 尾-ketonitriles or isoxazoles with high chemoselectivity depending on the reaction conditions. The reaction of 尾-oxodithioesters with hydroxylamine in EtOH at room temperature in daylight gave 尾-ketonitriles in high yields. On the other hand, 3-methylthio-isoxazoles were efficiently obtained as the final products by heating the mixture of 尾-oxodithioesters and hydroxylamine in HOAc at 90 掳C.