Base-catalyzed protium–deuterium exchange in bicyclo[2.2.1]heptanones Theses uri icon

  •  
  • Overview
  •  
  • Research
  •  
  • View All
  •  

abstract

  • The rates of NaOD-catalyzed protium–deuterium exo exchange in fenchan-2,5-dione (2) and 1-methyl-5-oxo-camphene (3) are 200 and 7, respectively, relative to epiisofenchone (1). The endo exchange rates in 2 and 3 are 1840 and 4, respectively, relative to 1. These data give information about the relative importances of conjugative, conformational, inductive, strain, and steric effects which may arise when a carbonyl group or a double bond is situated 1,3 to an enolizable center in the 2.2.1 system.

publication date

  • December 15, 1970