Chinese Journal of Organic Chemistry >
Preparation of α,α'-Bismethylenyl Zirconacyclopentane and Its Application in the Synthesis of 1,5-Hexadiene Derivatives
Received date: 2014-12-31
Revised date: 2015-01-25
Online 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).
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.
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]. Chinese Journal of Organic Chemistry, 2015 , 35(3) : 662 -671 . DOI: 10.6023/cjoc201412058
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