γ-Deuterium Isotope Effects on Solvolysis of 7-Halonorbornyl Brosylates-6-d Journal Articles uri icon

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abstract

  • The γ-deuterium isotope effects for the solvolysis of anti- and syn-7-chloro-, anti- and.syn-7-bromo-exo-2-norbornyl brosylates-6-endo-d and.syn-7-chloro-exo-2-norbornyl brosylate-5,6-exo,exo-d2 in 80:20 EtOH–H2O, 0.04 M NaOAc at 65° are 1.11 ± 0.01, 1.11 ± 0.01, 1.13 ± 0.01, 1.05 ± 0.01, and 1.11 ± 0.01, respectively. The results indicate that the γ-isotope effect observed in the solvolysis of exo-norbornyl brosylate likely is not derived via neighboring group (non-vertical) participation of the C1—C6 bond.

publication date

  • October 15, 1973