A simple procedure for C-C bond cleavage of aromatic and aliphatic epoxides with aqueous sodium periodate under ambient conditions |
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| Authors: | Caitlin M. Binder Erik Almaraz Bakthan Singaram |
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| Affiliation: | a University of California, Santa Cruz, 1156 High Street, Santa Cruz, CA 95064, United States
b Department of Chemistry, 2545 The Mall, University of Hawaii, Honolulu, HI 96822, United States |
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| Abstract: | 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. |
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