Regioselective Opening of Simple Epoxides with Diisopropylamine Trihydrofluoride

Article abstract of DOI:10.1021/jo00240a017

Treatment of benzyl ether derivatives of simple aliphatic epoxy alcohols with diisopropylamine trihydrofluoride gave mixtures of the corresponding fluorohydrins in good yields.Steric hindrance is a major factor in determining the regioselectivity of epoxide opening, although electronic effects cannot be ignored.Electronic effects are more dominant with pyridine polyhydrofluoride.