28987-55-5Relevant academic research and scientific papers
Reactions of aromatic compounds with nucleophilic reagents in liquid ammonia: XVII. Effect of ionic association on the orientation in aryloxydefluorination of 2,4-difluoronitrobenzene
Politanskaya,Ryabitskaya,Malykhin,Steingartz
, p. 801 - 807 (2007/10/03)
The analysis of dependence of fluorine replacement orientation in 2,4-difluoronitrobenzene effected by nucleophiles Y-C6H4OM (Y = p-OMe, p-Me, m-Me, H, p-F, p-Cl, m-F, m-Cl; M = Li, Na, K, Et4N, Bu4N) in liquid
Reaction of Aromatic Compounds with Nucleophilic Reagents in Liquid Ammonia. XIV. Effect of Liquid Ammonia as Solvent on the Orientation of Phenoxydefluorination of 2,4-Difluoronitrobenzene by Substituents in the Nucleophile
Politanskaya,Malykhin,Shteingarts
, p. 1131 - 1142 (2007/10/03)
A relation is revealed between the orientation of fluorine substitution in 2,4-dinitrofluorobenzene (ortho/para ratio) by phenoxy group under the action of X-substituted lithium phenoxides (X = H, p-Me, m-Me, p-OMe, p-F, p-Cl, m-Cl, m-F) in liquid ammonia at -35 to -33°C and the nature of substituent X. Comparison of log (ortho/para) with values of -δΔG0 = ΔG0H - ΔG1X, which characterize the effect of substituent X on the Gibbs energies of protonation of substituted phenoxides in the gas phase and aqueous and DMSO solutions, together with the data on the relative contributions of various components of substituent effect in the title reaction, shows that liquid ammonia behaves like aprotic dipolar solvent.
