Tetrahedron letters

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

…, DD Dixon, E Almaraz, MA Tius, B Singaram

文献索引：Binder, Caitlin M.; Dixon, Darryl D.; Almaraz, Erik; Tius, Marcus A.; Singaram, Bakthan Tetrahedron Letters, 2008 , vol. 49, # 17 p. 2764 - 2767

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被引用次数: 33

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.