30557-82-5Relevant academic research and scientific papers
Rates of Acid- and Base-Catalyzed Enolization of trans-Hexahydrofluorenone. Concerning Stereoelectronic Control of Enolization
Pollack, Ralph M.,Kayser, Robert H.,Cashen, Michael J.
, p. 3983 - 3987 (1984)
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.
The effect of electrochemically formed aluminum salts on the electrochemical cyclisation of methyl cinnamate
Guellue, Mustafa
, p. 3225 - 3228 (2007/10/03)
Electrochemical cyclisation of methyl cinnamate with dielectrophiles has been improved by the presence of an aluminum salt which was pre-formed in situ by the electrolysis of a carboxylic acid with a sacrificial aluminum anode. High yields of three, five and six-membered cyclic products have been obtained in the reactions of methyl cinnamate with dichloromethane, 1,3- dibromopropane, and 1,4-dibromobutane.
