Rates of acid-and base-catalyzed enolization of trans-hexahydrofluorenone. Concerning stereoelectronic control of enolization

RM Pollack, RH Kayser, MJ Cashen

Index: Pollack, Ralph M.; Kayser, Robert H.; Cashen, Michael J. Journal of Organic Chemistry, 1984 ,  vol. 49,  # 21  p. 3983 - 3987

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Citation Number: 5

Abstract

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 ...