Defense Date

6-30-2023

Graduation Date

Summer 8-5-2023

Availability

One-year Embargo

Submission Type

dissertation

Degree Name

PhD

Department

Chemistry and Biochemistry

Committee Chair

Thomas D. Montgomery

Committee Member

Jeffrey D. Evanseck

Committee Member

Paul A. Lummis

Committee Member

Patrick T. Flaherty

Keywords

heterocyclics, 1, 2-diamines, vicinal diamines, imidazolidines, pyrrolidines, cycloadditions

Abstract

Nitrogen containing compounds are ubiquitous in nature as well as pharmaceuticals. These structures exhibit rich bioactive and chemical properties boasting an array of practical applications. As a result, the synthetic methods of forming nitrogen containing compounds are highly sought after. More efficient syntheses of these structures could result in less expensive industrial processes, particularly in the pharmaceutical industry. Roussi and coworkers established a highly efficient synthetic route forming nitrogen containing heterocycles in a single step from commercially available reagents, however this chemistry has not be used since its discovery in the 1980. Herein, this work greatly expanded Roussi’s method and developed a new route accessing vicinal diamines as well as nitrogen containing heterocycles.

Allenes are also important motifs present in natural products and some pharmaceuticals. Moreover these compounds are useful building blocks for synthetic scaffolds because they exhibit unique reactivities forming complex products from one-step transformations. The synthetic methods of forming allenes typically suffer from multiple steps and harsh reagents. This work focused on developing a mild synthetic method of forming substituted allenes using a nickel catalyzed process.

Language

English

Additional Citations

Hejnosz, S. L.; Beres, D. R.; Cocolas, A. H.; Neal, M. J.; Musiak, B. S.; Hanna, M. M. B.; Bloomfield, A. J.; Montgomery, T. D. [3 + 2] Cycloadditions of Tertiary Amine N-Oxides and Silyl Imines as an Innovative Route to 1,2-Diamines. 2023. https://doi.org/10.1021/acs.orglett.3c01396.

Neal, M. J.; Hejnosz, S. L.; Rohde, J. M.; Evanseck, J. D.; Montgomery, T. D. Multi-Ion Bridged Pathway of N-Oxides to 1,3-Dipole Dilithium Oxide Complexes. 2021, 86 (17), 11502–11518. https://doi.org/10.1021/acs.joc.1c01047.

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