- Synthesis of α-iodo-α,β-unsaturated ketones by the reaction of α- silyl-α,β-unsaturated ketones with ICl or ICIl-AlCl3
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Treatment of α-silyl-α,β-unsaturated enones, readily preparable as regio- and stereodefined compounds in high yields, with either 2 equiv, of ICl or one equiv, each of ICl and AlCl3 provides the corresponding α-iodo- α,β-unsaturated enones in h
- Alimardanov, Asaf,Negishi, Ei-ichi
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p. 3839 - 3842
(2007/10/03)
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- Solvent-free organic reactions on silica gel supports. Facile transformation of epoxides to β-halohydrins with lithium halides
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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.
- Kotsuki, Hiyoshizo,Shimanouchi, Tomoyasu,Ohshima, Reiji,Fujiwara, Shunsuke
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p. 2709 - 2722
(2007/10/03)
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- A facile conversion of epoxides to β-halohydrins with silica gel-supported lithium halides
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A variety of epoxides are efficiently converted to the corresponding β-halohydrins with lithium halides supported on silica gel in dry media.
- Kotsuki, Hiyoshizo,Shimanouchi, Tomoyasu
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p. 1845 - 1848
(2007/10/03)
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