Carbonate ester
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A carbonate ester is a functional group in organic chemistry consisting of a carbonyl group flanked by two alkoxy groups. The general structure of these carbonates is R1O(C=O)OR2 and they are related to esters R1O(C=O)R and ethers R1OR2 and also to the inorganic carbonates.
Carbonate esters are used as protecting group for diols. A classic reagent is phosgene but more user friendly reagents exist such as carbonyl diimidazole. Ethylene carbonate and Propylene carbonate are used as a solvent. Dimethyl carbonate is used as a methylating reagent.
In many applications a carbonate group replaces an ester group for example in Cholesteryl oleyl carbonate. Polycarbonates are an important class of polymers.
[edit] Organic synthesis
Laboratory methods for the synthesis of carbonate ester in the laboratory are:
- from the corresponding diols.
- by double oxidation of ketones in a Baeyer-Villiger rearrangement
- by reaction of an epoxide with carbon dioxide catalysed by a zinc halide [1]
[edit] References
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