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A novel method for constructing a 7-oxabicyclo[2.2.1]heptane skeleton was developed. The substrates, namely cis-3,4-epoxy-1-cyclohexanol derivatives, were prepared from the corresponding 3-cyclohexen-1-ol derivatives via a stereoselective epoxidation reaction using a vanadium catalyst. Upon heating with lithium iodide in propionitrile, the cis-epoxy alcohol was transformed into the 7-oxabicyclo[2.2.1]heptane derivative in high yield. The reaction proceeds through formation of a lithium alkoxide bearing an iodohydrin moiety, followed by an intramolecular SN2 reaction. 相似文献
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Karen S. M. Corrêa Marcio C. S. de Mattos Mônica R. M. P. de Aguiar 《Monatshefte für Chemie / Chemical Monthly》2009,140(5):519-522
Abstract Styrene oxide is easily prepared in 82–91% yield by the reaction of styrene with iodine/water in the presence of commercial
clays, followed by in situ addition of KOH in n-hexane/water.
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