Investigation of Keto-enol Tautomers during the Synthesis of Aryl-bis (2-hydroxy-1-naphthyl)Methanes

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• 作者：PAPIA DUTTA (1)
  MRINAL SAIKIA (1)
  RASHMI JYOTI DAS (1)
  RULI BORAH (1)
  
• 关键词：Aryl ; bis(2 ; hydroxy ; 1 ; naphthyl)methanes ; keto ; enol tautomer ; CuSO4.5H2O ; .BF3.OEt2/acetic acid
• 刊名：Journal of Chemical Sciences
• 出版年：2014
• 出版时间：November 2014
• 年：2014
• 卷：126
• 期：6
• 页码：1629-1634
• 全文大小：306 KB
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• 作者单位：PAPIA DUTTA (1)
  MRINAL SAIKIA (1)
  RASHMI JYOTI DAS (1)
  RULI BORAH (1)
  
  1. Department of Chemical Sciences, Tezpur University, Napaam, 784028, Tezpur, Assam, India
  
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry
  Chemistry
  
• 出版者：Springer India
• ISSN：0973-7103

文摘

This study investigated the existence of keto-enol tautomers for the first time during the synthesis of aryl-bis(2-hydroxy-1-naphthyl)methane from 2-naphthol and p-tolualdehyde or 4-chlorobenzaldehyde in methanol using CuSO4.5H2O as catalyst under reflux condition. The exclusive formation of aryl-bis(2-hydroxy-1-naphthyl)methanes was observed in dichloromethane at room temperature in the presence of BF3.OEt2/AcOH as catalyst. The keto products were isolated and characterized by 1H NMR, 13C NMR, COSY and DEPT spectra. Graphical Abstract The existence of keto tautomer (3) of aryl-bis (2-hydroxy-1-naphthyl)methanes (4) was identified in the reaction of 2-napthol with p-tolualdehyde and 4-chlorobenzaldehyde using CuSO4.5H2O as catalyst under reflux in methanol. Exclusive formations of (4) was observed at mild conditions in dichloromethane with BF3.OEt2/AcOH as catalyst.