Synthesis of cyclic sulfonamides by reaction of N-sulfinyl-3-(trifluoromethyl)aniline with norbornenes

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• 作者：Ya. V. Veremeichik ; D. N. Shurpik…
• 刊名：Russian Journal of Organic Chemistry
• 出版年：2016
• 出版时间：January 2016
• 年：2016
• 卷：52
• 期：1
• 页码：92-95
• 全文大小：385 KB
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• 作者单位：Ya. V. Veremeichik (1)
  D. N. Shurpik (2)
  O. A. Lodochnikova (3)
  V. V. Plemenkov (1)
  
  1. Immanuel Kant Baltic Federal University, ul. Universitetskaya 2, Kaliningrad, 236040, Russia
  2. Butlerov Institute of Chemistry, Kazan (Volga Region) Federal University, Kremlevskaya ul. 18, Kazan, 420088, Tatarstan, Russia
  3. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, ul. Arbuzova 8, Kazan, 420088, Tatarstan, Russia
  
• 刊物主题：Organic Chemistry;
• 出版者：Springer US
• ISSN：1608-3393

文摘

N-Sulfinyl-3-(trifluoromethyl)aniline reacted with bicyclo[2.2.1]hept-2-ene and bicyclo[2.2.1]-hepta-2,5-diene to give the corresponding Diels‒Alder adducts which were oxidized to 8-trifluoromethyl-2,3,4,4a,6,10b-hexahydro-5λ 6-1,4-methanodibenzo[c,e][1,2]thiazine-5,5(1H)-diones. The cycloaddition occurred predominantly with participation of the S=N–C1=C6 fragment of N-sulfinyl-3-(trifluoromethyl)aniline and exclusively at the endo side of bicyclo[2.2.1]heptenes.