Base-catalyzed protium–deuterium exchange in bicyclo[2.2.1]heptanones
- 15 December 1970
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 48 (24) , 3966-3967
- https://doi.org/10.1139/v70-666
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.Keywords
This publication has 0 references indexed in Scilit: