B. Man, J. Hook, J. Harper
Oct 31, 2005
Citations
0
Influential Citations
63
Citations
Journal
Tetrahedron Letters
Abstract
Abstract The rate of the substitution reaction of ( R )-3-chloro-3,7-dimethyloctane ( 1 ) with either methanol or benzyl alcohol in mixtures containing the ionic liquid [Bmim][N(CF 3 SO 2 ) 2 ] was monitored using 35 Cl NMR spectroscopy. The enantiomeric excess of the product, ( S )-3-methoxy-3,7-dimethyloctane ( 2a ), was analyzed using chiral gas chromatography. This product showed a decreasing enantiomeric excess with increasing concentration of ionic liquid. The rate of reaction of substrate 1 in each case varied with the concentration of the ionic liquid. Polarity measurements of the solvent mixtures were undertaken by standard methods, which are compared both to each other and to the observed rates. Solvent reorganization and selective solvation are also each proposed as contributing to the difference in the observed rates of reaction.