Russian Journal of Organic Chemistry

, Volume 38, Issue 4, pp 553–563 | Cite as

New N-(Arylsulfonyl)-5-aminomethylbicyclo[2.2.1]hept-2-enes. Synthesis, 1H and 13C NMR Spectra, and Chemical Reactions

  • A. O. Kas'yan
  • A. K. Isaev
  • L. I. Kas'yan
Article

Abstract

A synthesis of new N-(arylsulfonyl)-5-aminomethylbicyclo[2.2.1]hept-2-enes obtained by reaction of stereoisomeric exo- and endo-5-aminomethylbicyclo[2.2.1]hept-2-enes with arylsulfonyl chlorides is described. With the use of the data of 1H and 13C NMR spectra, including those of two-dimensional spectra recorded in COSY and NOESY mode, the contribution of stereochemical features of sulfonamides into the spectra structure of endo- and exo-isomers was evaluated. Applying various methods of the phase-transfer catalysis alkylation and acylation of the stereoisomeric arylsulfonamides containing a norbornene fragment was carried out. The reactions of alkylated stereoisomeric sulfonamides, N-(benzyl)-N-(3,4-dichlorophenylsulfonyl)-5-aminomethylbicyclo[2.2.1]hept-2-enes, with peroxyphthalic acid provide epoxides; the orientation of substituents in the cage norbornene fragment does not affect the direction of the process. The structure of the products obtained by sulfonamides transformations was confirmed by IR, 1H and 13C NMR spectra.

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Copyright information

© MAIK “Nauka/Interperiodica” 2002

Authors and Affiliations

  • A. O. Kas'yan
    • 1
  • A. K. Isaev
    • 2
  • L. I. Kas'yan
    • 2
  1. 1.Rein-Westfalen Technische UniversitaetAachen
  2. 2.Dnepropetrovsk State UniversityDnepropetrovskUkraine

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