1335333-86-2Relevant articles and documents
Anion-Initiated Trifluoromethylation by TMSCF3: Deconvolution of the Siliconate-Carbanion Dichotomy by Stopped-Flow NMR/IR
Johnston, Craig P.,West, Thomas H.,Dooley, Ruth E.,Reid, Marc,Jones, Ariana B.,King, Edward J.,Leach, Andrew G.,Lloyd-Jones, Guy C.
supporting information, p. 11112 - 11124 (2018/09/06)
The mechanism of CF3 transfer from R3SiCF3 (R = Me, Et, iPr) to ketones and aldehydes, initiated by M+X- (0.004 to 10 mol %), has been investigated by analysis of kinetics (variable-ratio stopped-flo
Mechanistic studies of the lithium enolate of 4-fluoroacetophenone: Rapid-injection NMR study of enolate formation, dynamics, and aldol reactivity
Kolonko, Kristopher J.,Wherritt, Daniel J.,Reich, Hans J.
supporting information; experimental part, p. 16774 - 16777 (2011/12/04)
Lithium enolates are widely used nucleophiles with a complicated and only partially understood solution chemistry. Deprotonation of 4-fluoroacetophenone in THF with lithium diisopropylamide occurs through direct reaction of the amide dimer to yield a mixed enolate-amide dimer (3), then an enolate homodimer (1-Li)2, and finally an enolate tetramer (1-Li)4, the equilibrium structure. Aldol reactions of both the metastable dimer and the stable tetramer of the enolate were investigated. Each reacted directly with the aldehyde to give a mixed enolate-aldolate aggregate, with the dimer only about 20 times as reactive as the tetramer at -120 °C.
