Periodate Cleavage of 1,2-Diols

Sn2

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1,2-Diols can be cleaved oxidatively with sodium periodate NaIO4(and lead tetraacetate) to form two carbonyl compounds in this case formaldehyde, and periodic acid. This proceeds via a cyclic transition state.

When preceeded by dihydroxylation with osmium tetroxide, the sequence is an alternative to ozonolysis of alkenes.

B. Sklarz, Q. Rev. Chem. Soc., 1967, 21, 3.

 

 

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