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Synthetic study on 2,2'-(1,4-phenylene)bis(3-alkyl-1H-inden-1-ones): the first application of a sodium enolate as a 'protecting group' in the Grignard reaction.

  作者 Pang, Mei-Li;Wang, Ying;Feng, Xiang-Qing;Chen, Yong;Han, Jie;Meng, Ji-Ben;  
  选自 期刊  Synthesis;  卷期  2008年-11;  页码  1725-1728  
  关联知识点  
 

[摘要]Fluorescent Brighteners, and Photographic Sensitizers) Section A new series of orange 2,2'-(1,4-phenylene)bis(3-substituted-1H-inden-1-ones) was prepd. and the dye structures were established by 1H and 13C NMR, IR, and HRMS spectroscopy. One mol. structure was further confirmed by single crystal X-ray crystallog. The synthetic mechanism was studied in detail. The key step involves the reaction of the Grignard reagent with the sodium enolate of 2,2'-(1,4-phenylene)bis[1H-indene-1,3(2H)-dione]. This is the first example of a sodium enolate being employed as the protecting reagent for a carbonyl group in the Grignard reaction.

 
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