On the Mechanism of Base-catalyzed Hydrogen Isotope Exchange in Cyclic Ketones Journal Articles uri icon

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abstract

  • The kinetics of H → D exchange in norcamphor (1) and of D → H exchange in norcamphor-3,3-d2 (6) have been determined. The rate ratio kexo/kendo drops from 661 in H → D exchange to 72 for D → H exchange. These data imply the presence of a dual mechanism for endo exchange and emphasize the importance of isotope effects in dictating exchange selectivity.

publication date

  • April 1, 1975