Gilbert, Thomas M.
B.S. (Bachelor of Science)
Department of Chemistry and Biochemistry
Using 1-hydrosilatrane allows for one-pot direct esterification of aldehydes under mild conditions. This is done by first reducing the aldehyde to an alcohol, and then acetic acid solvent converts the alcohol to the acetate ester. This is unusual, as most reducing agents interact with carboxylic acids to produce side products. Up to 99% conversion of starting aldehyde was observed. The method shows good functional group tolerance, only proving unsuccessful with aldehydes containing strong electron donating groups. A variety of esters were isolated by flash chromatography in yields of 24 – 92%.
James, Reuben R.; Herlugson, Sharon; Varjosaari, Sami E.; Skrypai, Vladislav; Adler, Marc Jordan; and Gilbert, Thomas M., "One-pot reductive acetylation of aldehydes using 1-hydrosilatrane" (2018). Honors Capstones. 852.
5 pages; 1 poster
Northern Illinois University
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