Journal of the Chemical Society. Perkin transactions I p. 609 - 616 (1993)
Update date:2022-08-04
Topics: Oxidation alkenes Cyclisation Mediated molecular oxygen β-keto esters Free-radical Manganese(II) (III)-mediated Free-radical cyclisation Hydrocarbons
Yamada, Takashi
Iwahara, Yoko
Nishino, Hiroshi
Kurosawa, Kazu
The reactions of substituted ethenes with β-keto esters in the presence of a mixture of manganese(II) and manganese(III) acetates, and molecular oxygen yielded substituted 1,2-dioxan-3-ols 3 in 14-95percent yields.Cobalt(III) acetate, potassium permanganate, lead(IV) acetate, copper(II) acetate, chromium(VI) trioxide, thallium(III) acetate, ammonium cerium(IV) nitrate and iron(III) perchlorate were also used in place of manganese(III) acetate.Effects on the product yields of substituents in the alkenes and β-keto esters have been examined and reaction mechanisms are discussed.
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