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Russian Journal of Organic Chemistry

, Volume 48, Issue 12, pp 1530–1535 | Cite as

Oxidative addition of trifluoromethanesulfonamide to cycloalkadienes

  • M. Yu. Moskalik
  • V. V. Astakhova
  • B. A. Shainyan
Article

Abstract

Reactions of trifluoromethanesulfonamide with cyclopentadiene, cyclohexa-1,3- and -1,4-dienes, cyclohepta-1,3,5-triene, and cycloocta-1,3-diene in the presence of t-BuOCl-NaI were studied. Trifluoromethanesulfonamide added at one double bond of cyclopentadiene and cyclohexa-1,3-diene in regio- and stereoselective fashion to give N-(5-iodocyclopent-2-en-1-yl)trifluoromethanesulfonamide and trans-N,N′-cyclohex-3-ene-1,2-diylbis(1,1,1-trifluoromethanesulfonamide), respectively. The reaction with cyclohexa-1,4-diene involved both isolated double bonds to produce N,N′-(2-chloro-5-iodocyclohexane-1,4-diyl)bis(1,1,1-trifluoromethanesulfonamide) which underwent halophilic reduction of the CHI group by the action of NaI and elimination of HCl, leading to N,N′-(cyclohex-2-ene-1,4-diyl)bis(1,1,1-trifluoromethanesulfonamide). Under analogous conditions, cyclohepta-1,3,5-triene was oxidized to benzaldehyde, while no reaction with trifluoromethanesulfonamide occurred.

Keywords

Diene Cyclopentadiene Trifluoro Sodium Iodide Methanesulfonamide 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Pleiades Publishing, Ltd. 2012

Authors and Affiliations

  • M. Yu. Moskalik
    • 1
  • V. V. Astakhova
    • 1
  • B. A. Shainyan
    • 1
  1. 1.Favorskii Irkutsk Institute of Chemistry, Siberian DivisionRussian Academy of SciencesIrkutskRussia

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