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Chemical structure of the carbonate ester group.

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.

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]

References

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