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

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.