The effect of solid and solution phase Lewis acids on acetal formation and the Diels-Alder reaction

Author

Chanda L. Elam

Date of Award

5-1997

Degree Type

Thesis

Degree Name

Master of Science

Major

Chemistry

Major Professor

George W. Kabalka

Committee Members

Richard Pagni

Abstract

Previous research has employed activated alumina as a catalyst for acetal formation. Although the alumina converted aldehydes to acetals in high yields, the conversion of ketones was poor. The goal of a portion of this thesis is to use B-bromoboronated alumina to convert aldehydes and ketones to acetals. A comparison of these results with previous research will determine the effectiveness of this catalyst on the conversion of ketones to acetals.

The second portion of this thesis will focus on the effect of solid and solution phase Lewis acids on the Diels-Alder reaction of methyl acrylate and trans-piperylene. Research by Inukai demonstrates that highly acidic Lewis acids such as aluminum trichloride readily catalyzed this reaction and yield a regioselective product in the process. The effectiveness of activated (dehydrated) and modified aluminas, as well as the catalyst lithium perchlorate in diethyl ether will determine which of these catalyst exhibits regioselective capabilities.

Recommended Citation

Elam, Chanda L., "The effect of solid and solution phase Lewis acids on acetal formation and the Diels-Alder reaction. " Master's Thesis, University of Tennessee, 1997.
https://trace.tennessee.edu/utk_gradthes/10512