Directed hydrogenation of sulphoxides and sulphones

Thesis

This thesis describes the synthesis of a number of hydroxy vinylsulphoxides and sulphones by a high pressure modification of the Baylis-Hillman reaction, together with their directed hydrogenation catalysed by rhodium catalysts. A detailed kinetic analysis of a number of the hydrogenation reactions carried out by numerical analysis is also presented.

Chapter 1 serves as an introduction to directed hydrogenation and the chemistry of sulphur containing compounds.

Chapter 2 details the synthesis of catalysts and substrates used in hydrogenation reactions. The use of high pressures to improve the performance of the Baylis-Hillman reaction is included.

Chapter 3 details the products and the selectivity obtained in the hydrogenation of hydroxy vinylsulphoxides and sulphones. The kinetic resolution of 3-phenyl-2-(phenylsulphonyl)- propene-3-ol using a DiPAMP rhodium catalyst is described.

Chapter 4 details the numerical analysis of the kinetics of the hydrogenation reactions of a number of hydroxy vinylsulphoxides and sulphones.

Authors: Price, D; Price, David

• Publication date: 1992
• DOI: 10.5287/ora-pm8yq2ava
• Type of award: DPhil
• Level of award: Doctoral
• Awarding institution: University of Oxford
• Language: English
• Subjects: Sulfoxides; Rhodium catalysts; Hydrogenation; Sulfones; Synthesis