Advances in hydrocarbon synthesis: 1. Progress in the living polyhomologation reaction: New monomers, catalysts and architectures 2. Progress in synthesis and evaluation of potential nestmate recognition cues of the Argentine Ant (Linepithema humile)

This dissertation describes advances in hydrocarbon synthesis in two main sections. The first section describes the expansion in utility of the polyhomologation reaction (1) to produce geminal cyclopropyl group containing polymers via novel copolymerization of tertiary ylides and primary ylides, (2) to evaluate novel blocking groups for the production of a single site or double site initiator/catalyst, and (3) to employ potential initiators/catalysts and termination reactions towards the synthesis of possible macrocyclic polymers. The second section describes the progress in synthesis of potential hydrocarbon nestmate recognition cues of the Argentine Ant (Linepithema humile ).;Chapter 1 introduces the polyhomologation reaction. The first part describes the background of the polyhomologation reaction. The mechanism of the polyhomologation reaction is compared to similar boron mediated reactions and the main characteristics of produced polymers are discussed. The use of monomers, initiators and termination reaction to achieve functional telechelic polymers are also reported.;Chapter 2 describes the co-polymerization of methyl ylide and tertiary cyclopropyl ylide to form a dl-cyclopropyl group containing polymer. Other cyclopropyl containing polymers and co-polymerization using polyhomologation are also discussed.;Chapter 3 describes the progress in the development of sulfur based blocking groups for the polyhomologation reaction to produce double or single site initiators/catalysts. Trends in migratory aptitudes of borane compounds and early blocking groups are discussed. The synthesis and blocking abilities of three initiators are reported.;Chapter 4 discusses the progress in the controlled synthesis of macrocyclic polymethylene. Two termination reactions were examined as potential key step in macrocyclic polymer synthesis. In addition silica surface attachment of polyhomologation initiator/catalyst is reported for the potential improvement of macrocyclic polymer purification.;Chapter 5 discusses the synthesis and preliminary results of potential hydrocarbon nestmate recognition cues of the Argentine Ant (Linepithema humile). The selection process and background of the targets is discussed. The syntheses of hydrocarbon cues with least 33 linear carbons and with at least one methyl branch are reported.