Rates of both acid-catalyzed and base-catalyzed enolization of trans-hexahydrofluorenone (trans-HHF) have been measured and compared with those for a variety of other ketones. It was found that trans-HHF enolizes substantidy faster than cyclohexyl phenyl ketone (CPK) in both acid (1800-fold) and base (2650-fold). This rate variation is thought to be due to two factors.(1) In trans-HHF the cleaving CH bond is held rigidly parallel to the? r orbital of the ...
