Publication Date


Document Type


First Advisor

Gilbert, Thomas M.||Adler, Marc Jordan, 1981-

Degree Name

Ph.D. (Doctor of Philosophy)

Legacy Department

Department of Chemistry and Biochemistry


Organic chemistry; Chemistry


1-Hydrosilatrane is an easily synthesized, stable, solid silane which can be made into an efficient reducing agent in the presence of a Lewis base, by taking advantage of the properties of hypervalent silicon. Due to the simplicity of use and handling, 1-hydrosilatrane has the potential to be an appealing alternative to other more widely used reducing agents. Aromatic and aliphatic ketones were readily reduced with 1-hydrosilatrane in the presence of potassium tert-butoxide. The discovery of diastereoselectivity in the reduction of menthone, a chiral ketone, led to enantioselective reductions of prochiral ketones using chiral Lewis base activators. Enantiomeric excesses of up to 86% were observed. It was also shown that 1-hydrosilatrane could act as a chemoselective reducing agent in the formation of tertiary amines via direct reductive aminations, in the absence of activator or solvent. Attempts were also made to take advantage of the steric properties of silicon protecting groups in meta-directing electrophilic aromatic substitution of phenols, leading to a one-pot synthesis of O-aryl carbamates.


Advisors: Thomas M. Gilbert; Marc J. Adler.||Committee members: Elizabeth Gaillard; Douglas Klumpp; Carol Thompson.||Includes illustrations.||Includes bibliographical references.


418 pages




Northern Illinois University

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