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通过醛与1,3 - 二羰基化合物的意外反应选择性形成螺二氢呋喃和环丙烷。

Selective formation of spiro dihydrofurans and cyclopropanes through unexpected reaction of aldehydes with 1,3-dicarbonyl compounds.

作者信息

Wang Guan-Wu, Gao Jie

机构信息

Hefei National Laboratory for Physical Sciences at Microscale and Department of Chemistry,University of Science and Technology of China, Hefei, Anhui 230026, PR China.

出版信息

Org Lett. 2009 Jun 4;11(11):2385-8. doi: 10.1021/ol900451d.

DOI:10.1021/ol900451d
PMID:19388701
Abstract

An efficient methodology for the oxidative addition reaction of various aldehydes with 5,5-dimethylcyclohexane-1,3-dione and 1,3-indandione to selectively afford spiro dihydrofuran and cyclopropane derivatives, promoted by molecular iodine and dimethylaminopyridine under mechanical milling conditions, has been demonstrated. The products were obtained in good to excellent yields. A possible mechanism of this unusual reaction process is proposed.

摘要

已证明一种有效的方法,即在机械研磨条件下,由分子碘和二甲基氨基吡啶促进,使各种醛与5,5 - 二甲基环己烷 - 1,3 - 二酮和1,3 - 茚二酮发生氧化加成反应,以选择性地得到螺二氢呋喃和环丙烷衍生物。产物的产率良好至优异。还提出了这种不寻常反应过程的可能机理。

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Org Lett. 2009 Jun 4;11(11):2385-8. doi: 10.1021/ol900451d.
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