Conjugation Studies: The Synthesis of Vinyl Aziridines through the aza-Darzens Reaction

Persistent Link:
http://hdl.handle.net/10150/596123
Title:
Conjugation Studies: The Synthesis of Vinyl Aziridines through the aza-Darzens Reaction
Author:
Youtsler, Taylor Andrew
Issue Date:
2015
Publisher:
The University of Arizona.
Rights:
Copyright © is held by the author. Digital access to this material is made possible by the University Libraries, University of Arizona. Further transmission, reproduction or presentation (such as public display or performance) of protected items is prohibited except with permission of the author.
Embargo:
10-Jul-2016
Abstract:
Aziridines, three membered heterocycles containing a nitrogen in the ring, are extremely valuable to synthetic organic chemistry, as subjecting these compounds to ring opening processes initiates further capabilities for the molecule. Additionally, aziridines themselves possess the capacity and characteristics suitable for pharmaceutical applications, increasing the interest and appeal for their synthesis. One of the approaches to the formation of these products is the aza-Darzens reaction between imines and brominated nucleophiles. The research presented here aims to analyze this technique, specifically between tert-butanesulfinimines and methyl (E)-4-bromo-3-methylbut-2-enoate. Within the context of the reaction mechanism, the pivotal step involves nitrogen on a sulfinimine enolate bonding to the gamma carbon of the nucleophile, effectively cleaving bromine and producing an aziridine. Investigation into the development of the aforementioned imines and nucleophile is also accomplished in this undertaking.
Type:
text; Electronic Thesis
Keywords:
Aziridine; Conjugation; Imine; Nucleophile; Chemistry; aza-Darzens
Degree Name:
M.S.
Degree Level:
masters
Degree Program:
Graduate College; Chemistry
Degree Grantor:
University of Arizona
Advisor:
Njarđarson, Jon T.

Full metadata record

DC FieldValue Language
dc.language.isoen_USen
dc.titleConjugation Studies: The Synthesis of Vinyl Aziridines through the aza-Darzens Reactionen_US
dc.creatorYoutsler, Taylor Andrewen
dc.contributor.authorYoutsler, Taylor Andrewen
dc.date.issued2015en
dc.publisherThe University of Arizona.en
dc.rightsCopyright © is held by the author. Digital access to this material is made possible by the University Libraries, University of Arizona. Further transmission, reproduction or presentation (such as public display or performance) of protected items is prohibited except with permission of the author.en
dc.description.release10-Jul-2016en
dc.description.abstractAziridines, three membered heterocycles containing a nitrogen in the ring, are extremely valuable to synthetic organic chemistry, as subjecting these compounds to ring opening processes initiates further capabilities for the molecule. Additionally, aziridines themselves possess the capacity and characteristics suitable for pharmaceutical applications, increasing the interest and appeal for their synthesis. One of the approaches to the formation of these products is the aza-Darzens reaction between imines and brominated nucleophiles. The research presented here aims to analyze this technique, specifically between tert-butanesulfinimines and methyl (E)-4-bromo-3-methylbut-2-enoate. Within the context of the reaction mechanism, the pivotal step involves nitrogen on a sulfinimine enolate bonding to the gamma carbon of the nucleophile, effectively cleaving bromine and producing an aziridine. Investigation into the development of the aforementioned imines and nucleophile is also accomplished in this undertaking.en
dc.typetexten
dc.typeElectronic Thesisen
dc.subjectAziridineen
dc.subjectConjugationen
dc.subjectImineen
dc.subjectNucleophileen
dc.subjectChemistryen
dc.subjectaza-Darzensen
thesis.degree.nameM.S.en
thesis.degree.levelmastersen
thesis.degree.disciplineGraduate Collegeen
thesis.degree.disciplineChemistryen
thesis.degree.grantorUniversity of Arizonaen
dc.contributor.advisorNjarđarson, Jon T.en
dc.contributor.committeememberNjarđarson, Jon T.en
dc.contributor.committeememberJewett, Johnen
dc.contributor.committeememberTomat, Elisaen
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