Physical Sciences and Mathematics Commons^™

Refinements In The Isomer Distribution And Relative Rate Of Sulfonation Of Toluene And Hydrochlorination Of Olefins With Stannic Chloride Catalyst, David George Guillot

Theses and Dissertations

The sulfonation of toluene at -12.5° C. with sulfur trioxide in liquid sulfur dioxide was found to give 10.03 ± 0.20 % ortho, 0.73 ± 0.20 % meta and 89.24 ± 0.20 % para isomers. This isomer distribution was determined by isotope dilution analysis using sulfur-35 enriched sulfur trioxide. After dilution of aliquots of the neutralized sulfonation mixture with pure sodium salts of each of the isomers prepared from the corresponding toluidines, the isomers were converted to the p-toluidine salts, purified by recrystallization, and counted by liquid scintillation counting. The relative rate of sulfonation of toluene compared to benzene was …

The Synthesis Of 4-Spiro-2-Aryloxazolines Of Potential Pharmacological Interest, Paul Waddell Collins

Theses and Dissertations

Numerous and diverse physiological actions are found among 2-oxazoline compounds. No reports of the synthesis or biological testing of 4-spiro-2-aryl-2-oxazolines were found in the literature. On the basis of the known pharmacological activities of certain aza- and diazaspirans, it was felt that 4-spiro-2-aryl-2-oxazolines should possess medicinal activity. In particular, it was reasoned that the combination in a bicyclic spiro structure of the 2-oxazoline ring with rings systems commonly found in synthetic antitussive compounds might result in active antitussive agents.

The aim of this research was the synthesis of a series· of 2-aryl-2-oxazoline-4-spirocyclopentanes and a series of 1'-methyl-2-aryl-2-oxazoline-4-spiro-4’-piperidines. Six members were …