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1979 (1)
1Author    Reiner Luckenbach, Nikolaus MüllerRequires cookie*
 Title    Zur elektrocyclischen Ringöffnung von Cyclopropylhalogeniden bei der Reaktion mit Natriumiodid in Aceton Electrocyclic Ring Opening of Cyclopropyl Halides in the Course of their Reaction with Sodium Iodide in Acetone  
 Abstract    Reaction of cyclopropyl halides with sodium iodide in acetone [i.e. under typical Sis-2-conditions), proceeds via ring opening to allylic systems finally yielding 1,5-hexadienes upon dimerisation; ring-retained products were not detected. Application of the Wood-ward-Hoffmann rules lends strong support to a cationic synchronous mechanism. This is also confirmed by kinetic measurements proving this reaction to be first order over all. The kinetic data are shown to fit the Hammett equation using cr-values for cyclopropyl bromides and o + -values for geminal cyclopropyl dichlorides, respectively. The validity of the Woodward-Hoffmann-De Puyrule (according to which in synchronous reactions leaving groups situated endo are strongly favored over those situated exo) is tested in corresponding experiments involving condensed ring systems. I. Zum Problem der nukleophilen Substitution an Cyclopropylsystemen In der vorliegenden Arbeit werden die Reaktionen von 2-phenylsubstituierten Cyclopropylhalogeniden unter typischen SN2-Bedingungen (Umsetzung mit Natriumiodid in Aceton) untersucht. Zunächst 
  Reference    Z. Naturforsch. 34b, 464—480 (1979); eingegangen am 10. August/19. Dezember 1978 
  Published    1979 
  Keywords    Ring Opening, Woodward-Hoffmann Rules, Allylic Cations, Dimerisation, 1, 5-Hexadienes 
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 TEI-XML for    default:Reihe_B/34/ZNB-1979-34b-0464.pdf 
 Identifier    ZNB-1979-34b-0464 
 Volume    34