Functionalisation of polystyrene using organolithium and organoboron reagents

• Main Author: Hou, D.
• Published: Swansea University 1997
• Subjects: 547.7
• Online Access: http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.637310

The thesis deals with the synthesis and applications of two different types of polystyrene-supported sulfonic acids and bis-(2,4,6, -triisopropylphenyl)boranes (abbreviated to ditripylboranes). Some new methods have been developed by using organolithium reagents. <B>Chapter 1</B> outlines the research project. <B>Chapter 2</B> introduces the synthesis and applications of polymer-supported catalysts and reagents. <B>Chapter 3</B> gives a brief review of the preparation of organolithium reagents and intermediates. <B>Chapter 4</B> discusses the preparation of benzyllithiums in general and reports a superior procedure for generation of benzyllithium and substituted benzyllithiums from the corresponding chlorides. <B>Chapter 5</B> reports a general and efficient method for the preparation of organic sulfonic acids by insertion of sulfur trioxide into the metal-carbon bond of organolithium compounds. This method can be used for preparation of both aliphatic and aromatic organic sulfonic acids in good yields. <B>Chapter 6</B> reports new syntheses of two different types of polystyrenesulfonic acids by use of reaction types developed as reported in Chapter 5. <B>Chapter 7</B> investigates the synthesis of organylditripylboranes and two different types of polymer-supported ditripylboranes. <B>Chapter 8</B> charts the formation and applications of alkylditripylhydroborates and polymer-supported ditripylhydroborates, which display high diastereoselectivity in the reduction of ketones.