一种用于合成富烯的高效催化方法。
An efficient catalytic method for fulvene synthesis.
作者信息
Coşkun Necdet, Erden Ihsan
机构信息
On leave from Uludag University, Department of Chemistry, 16059, Bursa, Turkey.
出版信息
Tetrahedron. 2011 Nov 11;67(45):8607-8614. doi: 10.1016/j.tet.2011.09.036.
Abstract
The effects of the nature and amount of base, substrate structure, amount of added water and solvent on the condensation of carbonyl compounds with cyclopentadiene in the presence of secondary amines were investigated. Based on these studies, a new efficient and green synthesis of fulvenes was developed.
摘要
研究了碱的性质和用量、底物结构、加水量和溶剂对在仲胺存在下羰基化合物与环戊二烯缩合反应的影响。基于这些研究，开发了一种新的富烯高效绿色合成方法。
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Tetrahedron Lett. 2009 May 20;50(20):2381-2383. doi: 10.1016/j.tetlet.2009.02.221.
2
Room temperature dynamic polymers based on Diels-Alder chemistry.基于狄尔斯-阿尔德化学的室温动态聚合物。
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3
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