Synthesis of danicalipin a precursors and cycloaddition chemistry towards the production of strained and energetic materials
Abstract/Contents
- Abstract
- This dissertation comprises two projects centered around cycloaddition chemistry towards the production of strained rings and other energy-rich compounds. The first is aimed towards developing methods for simple and scalable syntheses of useful pre-energetic materials. This research is conducted in collaboration with the Naval Air Weapons Station China Lake, the Army Research Lab at Aberdeen Proving Ground, and the Defense Advanced Research Projects Agency (DARPA). High energy materials are of significant interest for their ability to store and release energy, and are utilized in explosives, propellants, and pyrotechnics. Energetic materials for military applications must meet rigorous requirements regarding toxicity, volatility, density, and stability to storage. We aim to identify novel, low-cost materials or small molecules which could serve as energetic materials for military use. Moreover, we seek to identify energetic materials that can be accessed via simple and scalable synthetic methods. Specifically, this work focuses on the synthesis of novel isoxazole nitroxyethyl-nitramines (NENAs) and less precedented, highly strained fluoroladderenes. The second project involves the development of a novel cyclobutadiene equivalent. Cyclobutadiene has been used in Diels--Alder reactions to form strained intermediates en route to synthetic target molecules such as cubane and (+)-asteriscanolide. Due to the anti-aromatic character and intrinsic instability of cyclobutadiene itself, several cyclobutadiene metal complexes have been developed. Cyclobutadieneiron tricarbonyl is the most commonly used metal complex, but its use requires a low-yielding multistep synthesis, toxic metal-carbonyl reagents, and harsh conditions to liberate the cyclobutadiene. Our goal is to develop a bench-stable cyclobutadiene equivalent for use in Diels--Alder reactions that can be accessed in a high-yielding and scalable manner, as well as a straightforward synthesis of analogs to make substituted cyclobutadienes.
Description
| Type of resource | text |
|---|---|
| Form | electronic resource; remote; computer; online resource |
| Extent | 1 online resource. |
| Place | California |
| Place | [Stanford, California] |
| Publisher | [Stanford University] |
| Copyright date | 2022; ©2022 |
| Publication date | 2022; 2022 |
| Issuance | monographic |
| Language | English |
Creators/Contributors
| Author | Cabrera, Gabrielle Elaine |
|---|---|
| Degree supervisor | Burns, Noah |
| Thesis advisor | Burns, Noah |
| Thesis advisor | Wandless, Thomas |
| Thesis advisor | Wender, Paul A |
| Degree committee member | Wandless, Thomas |
| Degree committee member | Wender, Paul A |
| Associated with | Stanford University, Department of Chemistry |
Subjects
| Genre | Theses |
|---|---|
| Genre | Text |
Bibliographic information
| Statement of responsibility | Gabrielle Cabrera. |
|---|---|
| Note | Submitted to the Department of Chemistry. |
| Thesis | Thesis Ph.D. Stanford University 2022. |
| Location | https://purl.stanford.edu/dz724xp2481 |
Access conditions
- Copyright
- © 2022 by Gabrielle Elaine Cabrera
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