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.