Aliphatic and simple cycloalkene epoxides fail to undergo transformation into fluorohydrins on treatment with hydrofluoric acid. A certain rigidity of the carbocyclic system is necessary for the reaction to be successful. Electron-withdrawing groups inhibit the ring-opening reactions even in rigid systems.
I. Shahak, Sh. Manor and E. D. Bergmann, J. Chem. Soc. C, 1968, 2129 DOI: 10.1039/J39680002129
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