Benign Catalysis and Expansion of Cyclobenzoins

Cyclobenzoins are a fledgling class of macrocycles first reported by the Miljanić group in 2015. Since the first reports, several modifications to the original two compounds, cyclotribenzoin and cyclotetrabenzoin, have been reported, but no developments on the production have been reported. Whether this is due to the use of sodium cyanide as a catalyst or the small substrate scope, this thesis aims to improve on both limitations. The first issue, the cyanide catalyst, presented an opportunity to develop a new method to synthesize cyclotetrabenzoin. After testing a series of N-heterocyclic carbene catalysts, a suitable alternative was determined. Initial results indicated a substantial drop in yield, but optimizing conditions brought the production from the N-heterocyclic carbene conditions into line with the cyanide-catalyzed conditions. Concerning the substrate scope, initial experiments suggested that the general poor solubility of the aromatic dialdehyde materials in the aqueous conditions prevented their use as cyclobenzoin precursors. Leveraging the newly developed N-heterocyclic carbenes, particularly the ability to utilize organic solvents, two completely novel cyclobenzoins were prepared and characterized.

Name thesis:degree_name

Master of Science

Level thesis:degree_level

Masters

Discipline thesis:degree_discipline

Chemistry

Grantor

University of Houston

Year dc:date.issued

2019

Author dc:creator

• Eisterhold, Andrew Michael 1990-

Advisor dc:contributor.advisor

• Miljanić, Ognjen Š.

Committee members dc:contributor.committeemember

• Daugulis, Olafs
• Harth, Eva M.
• Jacobson, Allan J.
• Krishnamoorti, Ramanan

• Cyclobenzoin
• Macrocycle
• Benzoin Condensation

Statement dc:rights

• The author of this work is the copyright owner. UH Libraries and the Texas Digital Library have their permission to store and provide access to this work. Further transmission, reproduction, or presentation of this work is prohibited except with permission of the author(s).

Language dc:language.iso

eng

Handle dc:identifier.uri

https://hdl.handle.net/10657/5552

OAI identifier oai:identifier

oai:uh-ir.tdl.org:10657/5552