β-keto carbonyl compounds are pharmaceutically relevant biomaterials. The preparation of such useful β-keto ester enolates, carboxylic acids and amides, is often accomplished with substituted ethyl chloroformate esters and strong bases. Hence, studies on carbonyl substitution chemistry to understand the influence of aqueous solvents on chemical reactivity of substituted ethyl chloroformates are pertinent. This undergraduate project analyzed (in detail) the solvent effects on ethyl-, 1-chloroethyl-, 2-fluoroethyl- and 2-benzyloxyethyl- chloroformates. Inductive effects due to the positioning of the substituent are shown to play crucial roles in the reaction chemistry of these esters. The solvent hydrogen-bonding ability also determines substrate reactivity and major reaction pathway.

Solvolytic mechanisms of common β-keto carbonyl compounds

251st National Meeting (2016)

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