Tetrahedron p. 2709 - 2722 (1998)
Update date:2022-07-29
Topics:
Kotsuki, Hiyoshizo
Shimanouchi, Tomoyasu
Ohshima, Reiji
Fujiwara, Shunsuke
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, presumably via halohydrin intermediates. The epoxide-opening reaction of (R)-(+)-styrene oxide was also investigated to clarify the stereochemical features of this reaction.
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