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1Author    Gabriele Wagner3, Uwe Verfürth, Rudolf Herrm, Carl KrügerRequires cookie*
 Title    Ring-Opening of (-)-Camphorsulfonim ide Derivatives and (+)-Fenchonesulfonimide by Nitronium Tetrafluoroborate  
 Abstract    Treating a derivative o f (-)-cam phorsulfonim ide (C A name: (3aS)-8,8-dimethyl-4,5,6,7-tetrahydro-3H -3a,6-m ethano-2,l-benzisothiazole 2,2-dioxide) or the isomeric (+)-fenchone-sulfonimide with nitronium tetrafluoroborate in acetonitrile does not lead to the expected products of cationic reactions, e.g. o f the Ritter reaction for halogenated compounds, but provokes a cleavage of the sulfonim ide group with the formation of a ring-opened product containing a sulfonyl fluoride and a nitroimine group. The reaction does occur only in the presence of solid nitronium tetrafluoroborate, but not after prior dissolution of the reagent. An X-ray structure of the product from (1 S)-3-e«rfo-bromocamphorsulfonimide confirms this unusual reaction. 
  Reference    Z. Naturforsch. 49b, 1150—1157 (1994); received March 30 1994 
  Published    1994 
  Keywords    Camphorsulfonimide, Nitronium Tetrafluoroborate, Ring Opening, Sulfonyl Fluoride, Nitroimine 
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 TEI-XML for    default:Reihe_B/49/ZNB-1994-49b-1150.pdf 
 Identifier    ZNB-1994-49b-1150 
 Volume    49