This Is AuburnElectronic Theses and Dissertations

Toward a Breathable Fabric for Protection Against Airborne Toxic Chemicals, and an Olefin-Forming Cascade Reaction En Route to 2,2’-Bi(glycerol)




Li, Xiaoxun

Type of Degree



Chemistry and Biochemistry


Part I. Several compounds that were envisioned to interact strongly with airborne chemical warfare agents, principally organophosphorus nerve agents, were synthesized. This was part of a multi-site, multi-investigator effort to make a breathable fabric that offered protection against airborne toxins. The compounds consisted of an “active protection element” and a linker moiety for attaching to the surface of the fabric. In our work, the active protection element was an aromatic carboxylic acid flanked by poly(ethylene glycol) sidechains. As the focus of the project shifted from nerve gases to toxic industrial chemicals, our strategy for countering the toxins shifted. We designed a multi-layer fabric with each porous layer surface-modified with a different reactive vi element. We found that attachment of compounds to the surface was highly satisfactory using the azide + alkyne click reaction. We prepared compounds to be used for creating an acidic porous layer, a basic porous layer, and an oxidative porous layer. Part II. 2,2’-bi(glycerol) or 2,3-bis(hydroxymethyl)-1,2,3,4-butanetetraol 73 is a new six-hydroxyl compound that is a potential precursor to novel dendrimers, unnatural lipids, and open framework coordination polymers. A synthesis of 73 in five steps and 18.9% overall yield was achieved. Starting from commercially available nitromethane, our synthesis makes 73 available in multigram quantities. A new olefin-forming cascade reaction for a nitrobromo compound was discovered. Treatment of 5-bromo-5-nitro-2,2-dimethyl-1,3-dioxane with NaH in various solvents leads in one step to 2,2,2',2'-tetramethyl[5,5']bi[1,3]dioxanylidene. The cascade reaction subsumes three separate steps, and gives a higher yield than the overall yield of the three steps separately.The X-ray crystal structure of 73 is reported.