高等学校化学学报

高等学校化学学报 ›› 1998, Vol. 19 ›› Issue (S1): 38.

• Organic Synthesis Chemistry • 上一篇    下一篇

A NEW Method for the Synthesis of Polyether Bridged Azulenes:Reactions of Conjugated Keto-carbenes in the Photolysis of the Corresponding Azulenoquinone Diazides

Yun-Shan Lin, Shuan-Ya Jiang, Shih-Jue Lin, Tian-Chuan Huang, Yuan L. Chow   

  1. Simon Fraser University, Burnaby, British Columbia, Canada and Tamkang University, Tamsui. Taiwan
  • 出版日期:1998-12-31 发布日期:1998-12-31

A NEW Method for the Synthesis of Polyether Bridged Azulenes:Reactions of Conjugated Keto-carbenes in the Photolysis of the Corresponding Azulenoquinone Diazides

Yun-Shan Lin, Shuan-Ya Jiang, Shih-Jue Lin, Tian-Chuan Huang, Yuan L. Chow   

  1. Simon Fraser University, Burnaby, British Columbia, Canada and Tamkang University, Tamsui. Taiwan
  • Online:1998-12-31 Published:1998-12-31

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摘要： Photolysis of 1,4-quinone diazides has been known to generate conjugated keto-carbenes that may exist in the triplet and singlet states of ground as well as lowest excited levels with energy levels closely packed to one another. We used the diazides of 1,3-disubstituted 2,4-azulenoquinones as the model compound to demonstrate their singlet state reactivity in electirophilic reactions in competition to other reactions. Under the optimum conditions, the keto-carbenes reacts with cyclic ethers or amines repetitively to give polyether bridged azulene derivatives.

Abstract: Photolysis of 1,4-quinone diazides has been known to generate conjugated keto-carbenes that may exist in the triplet and singlet states of ground as well as lowest excited levels with energy levels closely packed to one another. We used the diazides of 1,3-disubstituted 2,4-azulenoquinones as the model compound to demonstrate their singlet state reactivity in electirophilic reactions in competition to other reactions. Under the optimum conditions, the keto-carbenes reacts with cyclic ethers or amines repetitively to give polyether bridged azulene derivatives.

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