Alkyl chloroformates (ROCOCl) are esters of chloroformic acid that react with amines or ammonia to synthesize useful derivatives of carbamic acid (urethanes). Such derivatives are important in systemic insecticide synthesis and as wood and paint preservatives. Even though widely used, chloroformates in general, are federally listed as being very hazardous pollutants. Thus, it is important to comprehend the influences of aqueous solvent effects on chloroformate chemical compound structure and chemical reactivity. This project provides a framework to gauge the relationship between solvent effects and ethyl chloroformate substituent effects. We provide the 25 oC pseudo first-order kinetic data for 2-methoxyethyl-, 2-chloroethyl-, 2-fluoroethyl-, 1-chloroethyl- and ethyl chloroformate esters in a variety of pure and mixed binary aqueous-organic solvents. We confirm that dual bimolecular addition-elimination and unimolecular ionization channels occur in the solvolyses of the substituted ethyl chlroformate esters.

Comprehending the substituent and solvent effects in ethyl esters of chloroformic acid

255th National Meeting (2018)

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