The work of this thesis focuses on the further characterization of organic films that develop on the exterior and interior surfaces of windows in urban and rural areas. Previous work by our group has shown that these organic films contain organic contaminants (PAH, PCBs, OC pesticides, etc.), and air particulate material. Simulated precipitation experiments have shown that the organic film is easily washed off and that these contaminants enter surface waters, ultimately finding their way into sediments in rivers, lakes and oceans. Samples of organic films on windows were collected at numerous sites in the Toronto area between July 2000 and July 2001. Previous work led to the quantification of over 85 target analytes within these film samples including, n-alkanes, n-alkanoic acids, n-alkanoic diacids, unsaturated alkanoic acids, aromatic carboxylic acids and resin acids. Crude methanol extracts of these film samples were derivatized (MeONH2*HCl in pyridine, 37°C, 90 min. followed by N-trimethylsilyl-N-methyltrifluoroacetamide (MSTFA), 37°C, 30 min.) and analyzed by GC/MS in full scan EI+ mode. Twenty seven compounds were positively identified with authentic standards, showing excellent matches to mass spectra and retention index values. These compounds included sugars (arabinose, glucose, fructose, sucrose, trehalose), sugar alcohols (xylitol, pinitol, quebrachitol, inositols), acids (glyceric, benzoic, fumaric, succinic, malic, adipic, azelaic) and a number of other unidentified derivatives. A total of 103 unique peaks were observed in 12 window film samples. It appears that these compounds are of plant origin owing to the identification of plant sterols, β-sitosterol and stigmastanol. In addition, the wood combustion marker, levoglucosan, was identified in all but one film sample. The patterns of polar compounds identified in these films are similar to recent findings of these substances in air particulate. The profiles of these polar compounds in three Hamilton PM10 samples were similar to literature reports. The contribution of these newly identified compounds to the film exceeds or greatly exceeds the contribution of all previously identified chemical substances. There remains a significant amount of unidentified material in these films. The importance of these films lies in their pivotal role in the sequestering, transport and fate of organic contaminants in urban environments. / Thesis / Master of Science (MSc)

Conduritols have attracted a great deal of attention in recent years owing to biological activities exhibited by them and also their usefulness in the synthesis of other natural products and pharmaceuticals. Conduritols show interesting inhibitor activity for some glycosidases and serve as important intermediates in the synthesis of inositols. In this study, novel synthetic strategies leading to highly functionalized cyclohexene derivative containing an aromatic ring, namely phenyl-substituted conduritol was achieved successfully for the first time. As the starting material, substituted benzoquinone derivative, biphenyl-2-ol was used. Bromination of one double bond followed by the reduction of the carbonyl groups served the desired skeleton. Further substitution of the bromine atoms and functionalization of the remaining double bond opened up an entry for the synthesis of substituted conduritol and inositol derivatives. Moreover, by the use of hydroquinone as a starting material we developed new synthetic methodologies for the synthesis of another conduritol derivative, bromo-substituted conduritol for the first time. Oxidation of hydroquinone to the corresponding quinone followed by the bromination of one double bond gave the desired product. After the reduction of the carbonyl groups and protection of the hydroxyl groups, the key compound for the synthesis of bromo-substituted conduritol was obtained. As a result, we enabled to synthesize new conduritol derivatives and we had considerable advance for the synthesis of other conduritol derivatives, inositols and quercitols.