The Preparation and Acetolyses of 5-Deuteriated exo-2-Norbornyl-p-bromobenzenesulfonates Journal Articles uri icon

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abstract

  • The deuterionorborneols 2a, b, c, and e have been prepared and converted to the brosylates 1a, b, c, and e. The deuterium isotope effects determined spectrophotometrically for solvolysis in HOAc–KOAc are 1.00 ± 0.01, 1.01 ± 0.01, 0.99 ± 0.01, and 1.11 ± 0.01, respectively. These data establish that: (a) a steric deuterium isotope effect does not operate at C-5 and therefore probably not at C-6; (b) hyperconjugative stabilization of the norbornonium ion to the C-5 hydrogens is confirmed to be not important, and (c) provides the first experimental evidence that the hydrogen (deuterium) shift – internal return pathway contribution to the γ-deuterium isotope effects observed for 1d and e is minor.

authors

  • Werstiuk, Nick Henry
  • MacDonald, RR
  • Ouwehand, RW
  • Chan, WL
  • Cappelli, FP
  • Ballard, JG
  • Young, RE
  • Massey, RE
  • Timmins, G
  • Goodwin, I
  • Walling, A
  • Teruta, Miss Y

publication date

  • March 1, 1972