Journal of the American Chemical Society p. 5717 - 5722 (1985)
Update date:2022-07-30
Topics:
Farcasiu, Dan
Jaehme, Joachim
Ruechardt, Christoph
Heptafluorobutyrates, conveniently prepared from alcohols, possess a reactivity similar to that of halides in solvolysis reactions.A product and isotope distribution study for the reaction of 1-adamantyl heptafluorobutyrate (1a) in 80:20 ethanol-H2(18)O demonstrated exclusive alkyl-oxygen cleavage.The reactivities of 1a, 1-(2a), and 3-homoadamantyl heptafluorobutyrate (3a) increase with the flexibility of the hydrocarbon skeleton.The rate constants are linearly correlated with the strain increase upon ionization.No acceleration attributable to nucleophilic solvent assistance was evidenced for the tert-butyl ester, 4a.A literature proposal for such assistance in solvolyses of 4 is examined.The existing data are explained better by an SN1 process with electrophilic assistance of the leaving group in the solvents that can form very strong hydrogen bonds.
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