Study of dirhodium(II)-catalyzed hetero-Diels-Alder reactions: Investigations of diene influence and substitution pattern.

Persistent Link:
http://hdl.handle.net/10150/292084
Title:
Study of dirhodium(II)-catalyzed hetero-Diels-Alder reactions: Investigations of diene influence and substitution pattern.
Author:
Hedberg, Christine Michelle
Issue Date:
2005
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.
Abstract:
Studies pertaining to the dirhodium(II) carboxamidate catalyzed hetero-Diels-Alder reaction between 1-methoxy-2-methyl-3-(trimethylsilyloxy)-1,3-butadiene and various aldehydes have been carried out. It has been demonstrated that the overall yield, enantioselectivity, and rate of reaction for the hetero-Diels-Alder process are influenced by the substitution pattern of the diene. Collected data has allowed for the evaluation of the structural and electronic properties of the catalysts and for comparisons to be made between several dienes of interest. The complete synthesis of Rh₂(4R-dFIBAZ)₄, a dirhodium(II) carboxamidate catalyst that has shown increased reactivity for diazo decomposition and enhanced selectivity for ylide formation, has been previously reported by our group. Presented herein are the attempts taken to improve the existing synthesis through optimization and scale-up.
Type:
text; Thesis-Reproduction (electronic)
Keywords:
Chemistry, Organic.
Degree Name:
M.S.
Degree Level:
masters
Degree Program:
Graduate College; Chemistry
Degree Grantor:
University of Arizona
Advisor:
Doyle, Michael P.

Full metadata record

DC FieldValue Language
dc.language.isoen_USen_US
dc.titleStudy of dirhodium(II)-catalyzed hetero-Diels-Alder reactions: Investigations of diene influence and substitution pattern.en_US
dc.creatorHedberg, Christine Michelleen_US
dc.contributor.authorHedberg, Christine Michelleen_US
dc.date.issued2005en_US
dc.publisherThe University of Arizona.en_US
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_US
dc.description.abstractStudies pertaining to the dirhodium(II) carboxamidate catalyzed hetero-Diels-Alder reaction between 1-methoxy-2-methyl-3-(trimethylsilyloxy)-1,3-butadiene and various aldehydes have been carried out. It has been demonstrated that the overall yield, enantioselectivity, and rate of reaction for the hetero-Diels-Alder process are influenced by the substitution pattern of the diene. Collected data has allowed for the evaluation of the structural and electronic properties of the catalysts and for comparisons to be made between several dienes of interest. The complete synthesis of Rh₂(4R-dFIBAZ)₄, a dirhodium(II) carboxamidate catalyst that has shown increased reactivity for diazo decomposition and enhanced selectivity for ylide formation, has been previously reported by our group. Presented herein are the attempts taken to improve the existing synthesis through optimization and scale-up.en_US
dc.typetexten_US
dc.typeThesis-Reproduction (electronic)en_US
dc.subjectChemistry, Organic.en_US
thesis.degree.nameM.S.en_US
thesis.degree.levelmastersen_US
thesis.degree.disciplineGraduate Collegeen_US
thesis.degree.disciplineChemistryen_US
thesis.degree.grantorUniversity of Arizonaen_US
dc.contributor.advisorDoyle, Michael P.en_US
dc.identifier.proquest1427221en_US
dc.identifier.bibrecord.b49001164en_US
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