SON-DISSERTATION-2018.pdf (6.03 MB)
Download fileElectrocyclizations of N-Vinylnitrones and [3,3’]-Sigmatropic Rearrangement of N,O-Divinylhydroxylamines
thesis
posted on 2018-11-27, 00:00 authored by Jongwoo SonOur research group has developed new transformations involving N-vinylnitrone and N,O-divinylhydroxylamine intermediates to facilitate the synthesis of functionalized molecules and to access novel heterocyclic structures. Recently, we have expanded the scope of these methods to include the synthesis of oxazine-N-oxides through the 6π-electrocyclization of transient N-vinylnitrones, azetidine N-oxides through 4π-electrocyclization of N-vinylnitrones and the preparation of N-furanylamides through the addition of N,O-divinylhydroxylamines to electron-deficient allenes. The optimization, scope, and limitations of these new transformations will be discussed to emphasize new fundamental reactivity patterns and a detailed description of the synthetic versatility of these heterocyclic products will be presented to illustrate their utility in facilitating the preparation of sophisticated structures.
History
Advisor
Anderson, Laura LChair
Anderson, Laura LDepartment
ChemistryDegree Grantor
University of Illinois at ChicagoDegree Level
- Doctoral