Staff View
Development of amine alpha-functionalizations involving azomethine ylides intermediates

Descriptive

TitleInfo
Title
Development of amine alpha-functionalizations involving azomethine ylides intermediates
Name (type = personal)
NamePart (type = family)
Richers
NamePart (type = given)
Matthew Tracy
NamePart (type = date)
1987-
DisplayForm
Matthew Tracy Richers
Role
RoleTerm (authority = RULIB)
author
Name (type = personal)
NamePart (type = family)
Seidel
NamePart (type = given)
Daniel
DisplayForm
Daniel Seidel
Affiliation
Advisory Committee
Role
RoleTerm (authority = RULIB)
chair
Name (type = personal)
NamePart (type = family)
Knapp
NamePart (type = given)
Spencer
DisplayForm
Spencer Knapp
Affiliation
Advisory Committee
Role
RoleTerm (authority = RULIB)
internal member
Name (type = personal)
NamePart (type = family)
Williams
NamePart (type = given)
Lawrence J.
DisplayForm
Lawrence J. Williams
Affiliation
Advisory Committee
Role
RoleTerm (authority = RULIB)
internal member
Name (type = personal)
NamePart (type = family)
Wood
NamePart (type = given)
Harold B.
DisplayForm
Harold B. Wood
Affiliation
Advisory Committee
Role
RoleTerm (authority = RULIB)
outside member
Name (type = corporate)
NamePart
Rutgers University
Role
RoleTerm (authority = RULIB)
degree grantor
Name (type = corporate)
NamePart
Graduate School - New Brunswick
Role
RoleTerm (authority = RULIB)
school
TypeOfResource
Text
Genre (authority = marcgt)
theses
OriginInfo
DateCreated (encoding = w3cdtf); (qualifier = exact)
2015
DateOther (qualifier = exact); (type = degree)
2015-01
CopyrightDate (encoding = w3cdtf); (qualifier = exact)
2015
Place
PlaceTerm (type = code)
xx
Language
LanguageTerm (authority = ISO639-2b); (type = code)
eng
Abstract (type = abstract)
The α-functionalization of amines is a synthetic challenge of much interest to organic chemists. Common methods involve deprotonation with strong bases or oxidation with stoichiometric oxidants or transition metal catalysts. An alternative redox-neutral azomethine ylide-mediated approach to amine functionalization that harnesses the intrinsic reactivity of simple aldehyde and amine precursors without the need for harsh oxidants or bases will be detailed in this dissertation. The development of non-pericyclic amine annulations yielding aminal, N,O-acetal and N,S-thioacetal products will be discussed along with joint computational and experimental mechanistic studies on these reactions. The aminals are closely related to several naturally-occurring alkaloids and multiple methods were developed to synthesize these bioactive natural products and analogs. Additionally, two more azomethine ylide-based reactions will be discussed. The first is a variant on the classical Strecker reaction using α-amino acids which decarboxylatively gives rise to cyclic α-amino nitriles. Finally, a redox-neutral 1,5-electrocyclization reaction between secondary amines and α,β-unsaturated carbonyl compounds yielding amine heterocycles will be demonstrated.
Subject (authority = RUETD)
Topic
Chemistry and Chemical Biology
Subject (authority = ETD-LCSH)
Topic
Ylides
Subject (authority = ETD-LCSH)
Topic
Catalysts
RelatedItem (type = host)
TitleInfo
Title
Rutgers University Electronic Theses and Dissertations
Identifier (type = RULIB)
ETD
Identifier
ETD_6010
PhysicalDescription
Form (authority = gmd)
electronic resource
InternetMediaType
application/pdf
InternetMediaType
text/xml
Extent
1 online resource (xii, 491 p. : ill.)
Note (type = degree)
Ph.D.
Note (type = bibliography)
Includes bibliographical references
Note (type = statement of responsibility)
by Matthew Tracy Richers
RelatedItem (type = host)
TitleInfo
Title
Graduate School - New Brunswick Electronic Theses and Dissertations
Identifier (type = local)
rucore19991600001
Location
PhysicalLocation (authority = marcorg); (displayLabel = Rutgers, The State University of New Jersey)
NjNbRU
Identifier (type = doi)
doi:10.7282/T3H133RB
Genre (authority = ExL-Esploro)
ETD doctoral
Back to the top

Rights

RightsDeclaration (ID = rulibRdec0006)
The author owns the copyright to this work.
RightsHolder (type = personal)
Name
FamilyName
Richers
GivenName
Matthew
MiddleName
Tracy
Role
Copyright Holder
RightsEvent
Type
Permission or license
DateTime (encoding = w3cdtf); (qualifier = exact); (point = start)
2014-10-15 16:59:36
AssociatedEntity
Name
Matthew Richers
Role
Copyright holder
Affiliation
Rutgers University. Graduate School - New Brunswick
AssociatedObject
Type
License
Name
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.
Copyright
Status
Copyright protected
Availability
Status
Open
Reason
Permission or license
Back to the top

Technical

RULTechMD (ID = TECHNICAL1)
ContentModel
ETD
OperatingSystem (VERSION = 5.1)
windows xp
Back to the top
Version 8.5.3
Rutgers University Libraries - Copyright ©2024