Octyl chloroformate (OctOCOCl, 1) is used as a precursor for drugs that inhibit multiple enzymatic pathways to control obesity. The drug inhibits lipase which stops your body from breaking down and absorbing fat. Alkyl chloroformates in general are important precursors for many products and determining the mechanism of reaction for such subtrates is extensive and tedious work. Hence, this undergraduate research project is also funded through the DE-INBRE and DE-EPSCoR programs as it trains students in the basic methodologies. In this project, the acid-base titration method has been used to study the specific rates of 1 in different concentrations of aqueous acetone, aqueous ethanol (EtOH), aqueous methanol (MeOH), aqueous 1,1,1,3,3,3-Hexafluoroisoproponal (HFIP), aqueous 2,2,2, trifluoroethanol (TFE), and in mixtures of TFE-EtOH at 25.0 °C. For 1, the specific rates of solvolysis correlate well with an extended Grunwald-Winstein (G-W) treatment. A direct comparison to G-W analyses obtained for phenyl chloroformate (PhOCOCl) in identical solvents strongly suggests that the addition step within an addition-elimination mechanism is also favored in 1.

Using regression analysis to determine the mechanism of solvent reactions

249th National Meeting (2015)

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