The Journal of Organic Chemistry

Regioselective opening of simple epoxides with diisopropylamine trihydrofluoride

M Muehlbacher, CD Poulter

Index: Muehlbacher, Manfred; Poulter, C. Dale Journal of Organic Chemistry, 1988 , vol. 53, # 5 p. 1026 - 1030

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Citation Number: 49

Abstract

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.