108954-06-9Relevant academic research and scientific papers
Investigations into the C-deuteriation of aryl alkyl ketones using urea as a pro-base in the presence of a deuterium donor
Coumbarides, Gregory S.,Eames, Jason,Suggate, Michael J.,Weerasooriya, Neluka
, p. 641 - 652 (2007/10/03)
Results are reported on the regioselective C-deuteriation of a series of enolates derived from the deprotonation of aryl alkyl ketones using dilithiated urea as the pro-base in the presence of a suitable deuterium donor. Copyright
Investigations into the regioselective C-deuteration of acyclic and exocyclic enolates
Eames, Jason,Coumbarides, Gregory S.,Suggate, Michael J.,Weerasooriya, Neluka
, p. 634 - 641 (2007/10/03)
Results are reported on the regioselective C-deuteration of a series of related acyclic and exocyclic enolates derived from substituted aryl ketones. We comment on factors, such as the presence of additives and the structural nature of the enolate, that influence the observed C-deuteration and discuss the role of the deuterium donor. ( Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).
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 (2007/10/02)
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.
