Date of Award

6-1974

Document Type

Union College Only

Degree Name

Bachelor of Science

Department

Chemistry

Language

English

Abstract

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.

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