A study of the presence and impact of C-H()X- hydrogen bonds in phase-transfer catalysis

Abstract

In the first section are described our attempts at synthesizing a novel two centre phase-transfer catalyst. The various synthetic routes we undertook are illustrated as well as the problems that arose in each.* The second section summarizes our efforts towards demonstrating the existence of C-H hydrogen bonds in phase-transfer catalysts dissolved in organic solvents. These bonds had been shown to exist in the solid phase but no data regarding their presence under conditions resembling those encountered in phase-transfer catalyzed reactions had yet been gathered. In the third section, we attempted to study the potential effects of C-H hydrogen bonding in the phase-transfer catalyzed allylbenzene isomerization reaction. We compared the rate of reaction using both hydrogenated and deuterated phase-transfer catalysts.* *Please refer to dissertation for diagrams.