2,2,3,3,4,4,4 – Heptafluorobutyl chloroformate (C5H2ClF7O2) is used in treating conditions that are associated with diabetes as the compound aides in controlling the elevations of the beta-1 and beta-2 isozymes within the body. The protein kinase C isozymes, beta-1 and beta-2, can be inhibited within the body by 2,2,3,3,4,4,4 – heptafluorobutyl chloroformate. Hence, understanding the compound breakdown in solution is important. In this project, we followed the solvolysis of 2,2,3,3,4,4,4-heptafluorobutyl chloroformate and its parent, butyl chloroformate, in a series of binary aqueous organic mixtures with widely differing polarity. We found that in pure ethanol, the poly fluoro-substituted analog is 256 times faster than its parent butyl chloroformate and concluded that 2,2,3,3,4,4,4-heptafluorobutyl chloroformate follows an addition-elimination process in all solvents, including the highly ionizing TFE (2,2,2-trifluroethanol) and HFIP (1,1,1,3,3,3-hexafluro-2-propanol) mixtures. The large l/m (4.71) ratio for 2,2,3,3,4,4,4 – heptafluorobutyl chloroformate signifies that a much earlier tetrahedral transition state is occurring with a stronger general base catalysis (when compared to its parent).

Deactivating group substitution impacts on reaction rates

2019 Spring National Meeting

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