Journal of Organic Chemistry p. 3983 - 3987 (1984)
Update date:2022-08-05
Topics:
Pollack, Ralph M.
Kayser, Robert H.
Cashen, Michael J.
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 substantially 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 C-H bond is held rigidly parallel to the ? orbital of the ketone.About a factor of 25- to 60-fold is attributed to this stereoelectronic effect. (2) There are stericinteractions in the enol of CPK which decrease its rate of enolization by about 40- to 50-fold.
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Doi:10.1039/J39710000103
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