Abstract: Three compounds were synthesized each possessing rigid carbon frameworks that hold an oxygen base near a mobile CH proton in well-defined angular and distance relationships: 2-iodc-4-hydroxyindan, end&-hydroxybicyclo [2.2. 1] heptan-2-one, and endo- 2-hydroxy-exo-6-bromomethyl [2.2. 1] heptane. Effective proton transfer was detected with the second and third compounds but not the first. The data suggest that C-to-0 proton ...
