一重項酸素を用いる有機合成

概要

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The reactions of singlet oxygen with olefins can be classified into three categories ; (1) “ene” reaction to give allylic hydroperoxides, (2) 1, 4-cycloaddition to form 3, 6-dihydro-1, 2-dioxins, and (3) 1, 2- cycloaddition to give dioxetanes which are easily decomposed into two carbonyl compounds. “Ene” reaction has been used for the syntheses of allylic alcohols and α, β-unsaturated carbonyl compounds and also for the oxidative cleavage of double bonds. By the use of 1, 4-cycloaddition, both terminal carbons of 1.3-diene moiety were functionalized simultaneously and thus the resulting 1, 4-endo peroxides could be converted into various compounds such as furans, pyrroles, <I>cis</I>-2-butene-1, 4-diols, 1, 4-butanediols, and diepoxides. The 1, 2-cycloaddition has been applied to the syntheses of alpinine, alpigenine, and a musk fragrance. The reactions of singlet oxygen with sulfides and alkoxide anions may provide new preparative routes to sulfoxides and ketones.
社団法人有機合成化学協会の論文