Date of Award

8-31-2018

Document Type

Campus Access Thesis

Degree Name

Master of Science (MS)

Department

Chemistry/Organic Chemistry

First Advisor

Bela Torok

Second Advisor

Marianna Torok

Third Advisor

Jason Evans

Abstract

The development of three different synthetic protocols is described, each attempting to provide a greener synthetic alternative for existing reactions. First, a study on a modified Al-based hydrogenation system’s ability to perform reductions of various functional groups was conducted. The protocol was based on the combination of Pd/C-Al-H2O. The reaction of Al with water produced hydrogen gas in situ, that was utilized by the Pd/C hydrogenation catalyst. The reaction was carried out under mild conditions and resulted in excellent yields and selectivity. Second, the oxidative cleavage of styrenes using KSF montmorillonite, that represents a step towards replacing the harmful and dangerous ozonolysis reaction, was developed. Through the study of many catalysts and conditions it was found that KSF montmorillonite was able to perform the oxidative cleavage of styrenes resulting in the selective formation of benzaldehydes. Lastly, a mild synthesis of N-hydroxyalkylated indoles was developed. The chemo- and regioselectivity of the reaction is based on a specific solvent effect exhibited by non-protic and highly polar solvents such as DMSO which allowed for the selective N-hydroxyalkylation of several substituted indoles.

Comments

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