Preparation of α,α'-Bismethylenyl Zirconacyclopentane and Its Application in the Synthesis of 1,5-Hexadiene Derivatives

doi:10.6023/cjoc201412058

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (3): 662-671.DOI: 10.6023/cjoc201412058 Previous Articles Next Articles

ARTICLE

α,α'-双亚甲基锆杂环戊烷的构建及其在1,5-己二烯合成中的应用

胡麟峰, 王伟, 章彦婧, 林胜, 陆红燕, 郑卫新

杭州师范大学材料与化学化工学院杭州 310036

收稿日期:2014-12-31 修回日期:2015-01-25 发布日期:2015-01-28
通讯作者: 郑卫新 E-mail:wxzheng@hznu.edu.cn
基金资助:
国家自然科学基金(No. 20972037)、浙江省重点科技创新团队建设项目(No. 2010R50017)、杭州师范大学优秀中青年教师支持计划(No. HNUEYT-2011-01-013)、教育部创新团队长江学者和创新团队发展计划(No. IRT1231)资助项目.

Preparation of α,α'-Bismethylenyl Zirconacyclopentane and Its Application in the Synthesis of 1,5-Hexadiene Derivatives

Hu Linfeng, Wang Wei, Zhang Yanjing, Lin Sheng, Lu Hongyan, Zheng Weixin

College of Material, Chemistry & Chemical Engineering, Hangzhou Normal University, Hangzhou 310036

Received:2014-12-31 Revised:2015-01-25 Published:2015-01-28
Supported by:
Project supported by the National Natural Science Foundation of China (No. 20972037), the Special Funds for Key Innovation Team of Zhejiang Province (No. 2010R50017), the Excellent Young Teacher Support Program of Hangzhou Normal University (No. HNUEYT-2011-01-013) and the Program for Changjiang Scholars and Innovative Research Team in Chinese University (No. IRT1231).

1. Preparation of α,α'-Bismethylenyl Zirconacyclopentane and Its Application in the Synthesis of 1,5-Hexadiene Derivatives.PDF(1206KB)

Abstract

Zirconacycle has attached much attention owing to its various reactive behaviors. α,α'-Bismethylenyl zirconacyclopentane could be prepared by reductive coupling reaction of two 1,1-disubstituted allenes promoted by low covalent zirconocene species "Cp₂Zr (II)". The stereo- and regio-chemistry could be affected obviously by steric and electronic effect of the substituents in the allenes. Two sp² carbon-metallic bonds in α,α'-bismethylenyl zirconacyclopentane could be quenched by several electrophilic system and afford the novel methodologies for the synthesis of 1,1,6,6-tetrasubstituted 1,5-hexadiene, 2,5-dihalo-1,5-hexadiene and 1,6-dicarbonyl compound with the skeleton of 1,5-hexadiene.

Key words: α,α'-bismethylenyl zirconacyclopentane, 1,5-hexadiene, synthesis, selectivity

Cite this article

Hu Linfeng, Wang Wei, Zhang Yanjing, Lin Sheng, Lu Hongyan, Zheng Weixin. Preparation of α,α'-Bismethylenyl Zirconacyclopentane and Its Application in the Synthesis of 1,5-Hexadiene Derivatives[J]. Chin. J. Org. Chem., 2015, 35(3): 662-671.

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α,α'-双亚甲基锆杂环戊烷的构建及其在1,5-己二烯合成中的应用

Preparation of α,α'-Bismethylenyl Zirconacyclopentane and Its Application in the Synthesis of 1,5-Hexadiene Derivatives

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