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Development of amine functionalizations involving azomethine ylides
Descriptive
TitleInfo
Title
Development of amine functionalizations involving azomethine ylides
Name
(type = personal)
NamePart
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Ma
NamePart
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Longle
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Longle Ma
Role
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author
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Seidel
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Daniel
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Daniel Seidel
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Advisory Committee
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chair
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Williams
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Lawrence J.
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Lawrence J. Williams
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Advisory Committee
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internal member
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Warmuth
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Ralf
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Ralf Warmuth
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Advisory Committee
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internal member
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Wood
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Harold B.
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Harold B. Wood
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Advisory Committee
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Rutgers University
Role
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degree grantor
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Graduate School - New Brunswick
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Text
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theses
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2015
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2015-10
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2015
Place
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xx
Language
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eng
Abstract
(type = abstract)
Functionalization of amines is a very important research area in organic chemistry because functionalized amines are important building blocks in many biologically active compounds and pharmaceuticals. Outlined within this dissertation are our efforts toward the development of redox-neutral amine functionalizations involving azomethine ylides. The redox-neutral approach avoids unnecessary manipulations on the oxidation state of a targeted molecular structure. Therefore it has many advantages over conventional methods in which metal catalysts, oxidants or other additives are required. We discovered the isomerization of the iminium ion via the intermediacy of azomethine ylides. We took advantage of this unique reactivity and successfully developed the redox-neutral cyanation of amines and intramolecular Mannich reactions. This redox-neutral Mannich reaction was further applied to the syntheses of natural product thalicatricavine and its unnatural epimer. Furthermore, we have conducted mechanistic studies of the redox-neutral aromatization of amines and provided experimental evidence for several important intermediates proposed for this transformation. The synthetic utilities of some of the intermediates were explored. Lastly, a novel intermolecular hydride transfer triggered functionalization of amines was also investigated.
Subject
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Topic
Chemistry and Chemical Biology
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Title
Rutgers University Electronic Theses and Dissertations
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ETD_6593
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Note
Supplementary File: Appendix: Selected Spectra
Extent
1 online resource (xvii, 171 p. : ill.)
Note
(type = degree)
Ph.D.
Note
(type = bibliography)
Includes bibliographical references
Subject
(authority = ETD-LCSH)
Topic
Amines
Subject
(authority = ETD-LCSH)
Topic
Ylides
Note
(type = statement of responsibility)
by Longle Ma
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TitleInfo
Title
Graduate School - New Brunswick Electronic Theses and Dissertations
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rucore19991600001
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NjNbRU
Identifier
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doi:10.7282/T32F7QFC
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ETD doctoral
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Rights
RightsDeclaration
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The author owns the copyright to this work.
RightsHolder
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Name
FamilyName
Ma
GivenName
Longle
Role
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RightsEvent
Type
Permission or license
DateTime
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2015-06-30 15:51:57
AssociatedEntity
Name
Longle Ma
Role
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Affiliation
Rutgers University. Graduate School - New Brunswick
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Author Agreement License
Detail
I hereby grant to the Rutgers University Libraries and to my school the non-exclusive right to archive, reproduce and distribute my thesis or dissertation, in whole or in part, and/or my abstract, in whole or in part, in and from an electronic format, subject to the release date subsequently stipulated in this submittal form and approved by my school. I represent and stipulate that the thesis or dissertation and its abstract are my original work, that they do not infringe or violate any rights of others, and that I make these grants as the sole owner of the rights to my thesis or dissertation and its abstract. I represent that I have obtained written permissions, when necessary, from the owner(s) of each third party copyrighted matter to be included in my thesis or dissertation and will supply copies of such upon request by my school. I acknowledge that RU ETD and my school will not distribute my thesis or dissertation or its abstract if, in their reasonable judgment, they believe all such rights have not been secured. I acknowledge that I retain ownership rights to the copyright of my work. I also retain the right to use all or part of this thesis or dissertation in future works, such as articles or books.
RightsEvent
DateTime
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2015-10-31
DateTime
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2017-10-30
Type
Embargo
Detail
Access to this PDF has been restricted at the author's request. It will be publicly available after October 30th, 2017.
Copyright
Status
Copyright protected
Availability
Status
Open
Reason
Permission or license
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ETD
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windows xp
RULTechMD
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ETD
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