
TY  - JOUR
A1  - Angyal, SJ 
A1  - Evans, ME 
T1  - Oxidation of carbohydrates with chromium trioxide in acetic acid. IV. Conversion of cyclic methylene acetals into cyclic carbonates
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1972
VL  - 25
IS  - 7
SP  - 1513
EP  - 1520
KW  - 
UR  - https://doi.org/10.1071/CH9721513 
N2  - 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. 
ER  -

