o-benzoquinone photoreduction products in the presence of N,N-dimethylanilines

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• 作者：M. P. Shurygina ; Yu. A. Kurskii ; S. A. Chesnokov ; N. O. Druzhkov ; G. K. Fukin ; G. A. Abakumov and V. K. Cherkasov
• 关键词：photoreduction ; o ; benzoquinones ; N ; N ; dimethylanilines ; pyrocatechol monoethers
• 刊名：Russian Chemical Bulletin
• 出版年：2006
• 出版时间：September, 2006
• 年：2006
• 卷：55
• 期：9
• 页码：1585-1592
• 全文大小：449 KB
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry
  Chemistry
  Organic Chemistry
  Inorganic Chemistry
  Russian Library of Science
  
• 出版者：Springer New York
• ISSN：1573-9171

文摘

Photoreduction of o-benzoquinones in the presence of para-substituted N,N-dimethyl-anilines under irradiation at λ ≥ 500 nm affords pyrocatechol monoethers of the 2-(amino-methoxy)phenol type. In the subsequent dark reaction, these monoethers undergo quantitative decomposition by a heterolytic mechanism to give the corresponding pyrocatechols and nitrogen-containing compounds. The rate of this decomposition decreases with decreasing size of the substituent at the position adjacent to the ether bond that is formed upon photoreduction. The redox characteristics of such pyrocatechol monoethers can serve as the criterion of their stability. A weakening of the electron-withdrawing properties of quinones and the electron-donating properties of amines leads to an increase in stability of their reaction products.