The experimental results of the current work have three parts. First, the synthesis and characterization of several new copolymers by the free-radical copolymerization between several highly substituted electron-deficient olefins and furan, benzofuran, indene, alphamethylstyrene, and divinyl ether is discussed. Electron-poor olefins used included dimethyl cyanofumarate, carbomethoxymaleic anhydride and tricarbomethoxyethene. The spontaneous reactions of these monomer pairs were also investigated in both bulk and solution. Second, the effect of synthesis temperature on the composition of the previously reported (co)polymers of styrene with tricarbomethoxyethene and dimethyl dicyanofumarate are given. A ceiling temperature for the synthesis of this copolymer was found to be 220°C. Attempted copolymerization of tetracarbomethoxyethene gave evidence of a small but detectable amount of reaction. Finally, detailed procedures for the synthesis of dimethyl cyanofumarate, carbomethoxymaleic anhydride and tricarbomethoxyethene are given, including a new synthesis of carbomethoxymaleic anhydride.

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The objectives of this research problem was to employ alkylhaloketene-olefin isomer distributions to aid in understanding the stereochemistry and mechanism of alkylhaloketene-olefin cycloadditions.

Thesis advisor: James P. Morken / The metal-catalyzed diboration of alkenes has gained fame as a practical methodology for use in the stereoselective construction of complex organic molecules and synthetic building blocks. The created carbon-boron bonds have tremendous versatility and can easily be manipulated into carbon-carbon or carbon-heteroatom bonds. Unfortunately, metal-catalyzed diborations often suffer from limitations such as substrate specificity. To address these issues, we investigated diboration reactions in the absence of transition-metal catalysts. Herein is presented a transition-metal-free, diastereoselective diboration methodology utilizing alkenyl alcohols as substrates. Allylic alcohols can be treated with an organolithium base and bis(pinacolato)diboron to generate 1,2,3-triols upon oxidation. Most studies were done on homoallylic alcohols, which can be performed using a carbonate base and an alcohol additive. This methodology has many strengths, such as a wide substrate scope and high levels of diastereoselectivity. Further investigations into product functionalization and synthetic applications will be pursued in due time. / Thesis (MS) — Boston College, 2014. / Submitted to: Boston College. Graduate School of Arts and Sciences. / Discipline: Chemistry.

Thesis (Ph. D.)--University of Delaware, 2006. / Principal faculty advisor: Klaus H. Theopold, Dept. of Chemistry & Biochemistry. Includes bibliographical references.

Thesis (Ph.D.)--York University, 2004. Graduate Programme in Chemistry. / Typescript. Includes bibliographical references (leaves 167-179). Also available on the Internet. MODE OF ACCESS via web browser by entering the following URL: http://wwwlib.umi.com/cr/yorku/fullcit?pNQ99174

Thesis (Ph. D.)--University of Texas at Austin, 2000. / Vita. Includes bibliographical references (leaves 267-282). Available also in a digital version from Dissertation Abstracts.

Thesis (Ph. D.)--University of Texas at Austin, 2002. / Vita. Includes bibliographical references. Available also from UMI Company.