Tetrahedron

Solvent-free organic reactions on silica gel supports. Facile transformation of epoxides to β-halohydrins with lithium halides

H Kotsuki, T Shimanouchi, R Ohshima, S Fujiwara

Index: Kotsuki, Hiyoshizo; Shimanouchi, Tomoyasu; Ohshima, Reiji; Fujiwara, Shunsuke Tetrahedron, 1998 , vol. 54, # 12 p. 2709 - 2722

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Citation Number: 82

Abstract

The reaction of epoxides with lithium halides was efficiently promoted on the surface of silica gel in the absence of any solvent to give the corresponding β-halohydrins. The reactivity of lithium halides was shown to follow the order LiI> LiBr>> LiCl, and the reactivity of LiCl was dramatically increased by adding an equivalent amount of water to this system. On the other hand, a similar reaction with α, β-epoxyketones produces the α-haloenone derivatives, ...