Abstract
Addition of acetic
anhydride to the reagent, chromium trioxide in acetic acid, changes the outcome
of the oxidation of cyclic methylene acetals, giving
cyclic carbonates in addition to formyl ketones.
Five-membered acetals (acetylated 3,4-O-methylene-D-mannitol and-L-iditol) give good yields of the carbonates, which are
readily isolated as diisopropylidene derivatives.
Six-and seven-membered acetals (acetylated 2,4-O-methylene-D-glucitol and 2,5-O-methylene-D-mannitol) give poor yields of
carbonates, which are unstable under the acid conditions used for deacetylation: the carbonate group migrates or is removed.
Cited by
18 articles.
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