Facile endoperoxypropellane synthesis by manganese(III) acetate-mediated aerobic oxidation

被引：23

作者：

Asahi, Kentaro ^{[2
]}

Nishino, Hiroshi ^{[1
]}

机构：

[1] Kumamoto Univ, Grad Sch Sci & Technol, Dept Chem, Kumamoto 8608555, Japan

[2] Kumamoto Univ, Grad Sch Sci & Technol, Dept Mat & Life Sci, Kumamoto 8608555, Japan

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 2008卷 / 14期

关键词：

nitrogen heterocycles; peroxides; radicals; cyclization; oxidation;

D O I：

10.1002/ejoc.200701232

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Manganese (III)-catalyzed aerobic oxidation of combinations of 3-(2-oxoethyl)piperidine-2,4-diones and 1,1-diarylethenes at room temperature produced structurally interesting trioxaaza[4.4.3]propellanes in good yields. Similar reactions using 2-(2-oxoethyl)cyclohexane-1,3-diones also produced the corresponding endoperoxy[4.4.3]propellanes. On the other hand, 3-oxopropyl-substituted cycloalkane-1,3-diones did not give the desired propellanes, 1,2-dioxabicyclic propellane precursors were formed instead in excellent yields. The precursors could be converted into the corresponding propellanes in the presence of a Lewis acid. The mechanism for the formation of the propellanes is also described. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008).

引用

页码：2404 / 2416

页数：13

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