A simple procedure for C–C bond cleavage of aromatic and aliphatic epoxides with aqueous sodium periodate under ambient conditions

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• 作者：Caitlin M. Binder ; Darryl D. Dixon ; Erik Almaraz ; Marcus A. Tius ; Bakthan Singaram
• 关键词：Electoral bias ; Electoral geography ; Third parties
• 刊名：Tetrahedron Letters
• 出版年：2008
• 期刊代码：109_00404039
• 类别：ch
• 出版时间：21 April 2008
• 卷：49
• 期：17
• 页码：2764-2767
• 文件大小：122 K

摘要

The sodium periodate mediated oxidative cleavage of the C–C bond of 12 epoxides is reported with yields of the corresponding carbonyl compounds in up to 91%. This is a two-step reaction that proceeds through a rate-limiting epoxide opening to a vicinal diol that is cleaved in situ to the corresponding carbonyl compound. This method serves as a chemoselective alternative to ozonolysis.