The chemistry of triallylborane and 1-boraadamantane derivatives with dimethylsulfoxonium methylide and nitrogen-containing Lewis bases

This thesis is primarily concerned with the synthesis of trialkylboranes to react with dimethylsulfoxonium methylide (ylide) to form new polymethylene polymers. During the synthesis of reported trialkylboranes, such as triallylborane and 1-boraadamantane, the opportunity to design novel trialkylboranes and explore the chemistry of these reactive boranes with other substrates was also exploited. Chapter 1 concerns the characteristics of the reaction of trialkylboranes with ylide, in general. Chapter 2 concerns the synthesis of oligomeric linear alpha-olefins by the reaction of triallylborane with ylide followed by protolysis. Chapter 3 concerns the synthesis of 1-boraadamantane·THF to react with ylide to form regular star polymers with a cis, cis -1, 3, 5-substituted cyclohexane core. Chapter 4 concerns the application of 1-boraadalnantaneamine complexes for the design of antagonists for CD81, the surface cell receptor for hepatitis C. Chapter 5 explores the allylboron condensation reaction to form novel 2-spiro-1-boraaclamantane derivative. Finally, Chapter 6 explores the nature of the boron nitrogen bond in 1-boraadamantaneamine adducts and in 3-(dialkylboryl)-pyridine derivatives.