Date of Award
Union College Only
Bachelor of Science
Many aldehydes, ketones and other carbonyl-containing compounds react with 1, 2-ethanedithol to give highly stable cyclic thioacetals or thioketals. The problem lies in recovering the substituted 1, 3-dithiolanes to the carbonyl compound without altering the other substituents of the molecule. We propose a new direct method of exchange with formaldehyde to reconvert the 1, 3-dithiolane to the carbonyl compound. This was accomplished with 2, 2-diethyl-l, 3-dithiolane. Also, a mechanism is proposed involving the formation of a sulfonium ion intermediate. In preparation for the exchange study seven 1, 3-dithiolanes were synthesized.
Ginther, Jeffrey Paul, "The reconversion of ethylene thioketals to ketones" (1974). Honors Theses. 1813.