Online Archive of University of Virginia Scholarship
The Tungsten-Promoted Dearomatization of N-Sulfonyl Pyridinium Salts for Novel Organic Synthesis360 views
Author
Dabbs, Jonathan, Chemistry - Graduate School of Arts and Sciences, University of Virginia0009-0005-6310-4899
Advisors
Harman, Walter, AS-Chemistry (CHEM), University of Virginia
Abstract
This works describes the development of a second generation N-sulfonyl pyridinium dihapto bound to a WTp(NO)(PMe3) fragment. In addition to preserving the chemistry demonstrated by the first generation N-acetyl system without rotational isomers, this novel system demonstrated unprecedented reactivity pathways including a Zincke-like ring-opening of carbon substituted dihydropyridines and an acid-promoted scission of tetrahydropyridines. Additionally, these sulfonyl systems were applied in the synthesis of bicyclic alkaloids, piperidyl-substituted analogues of Ritalin, and deuterated tetrahydropyridines.
Dabbs, Jonathan. The Tungsten-Promoted Dearomatization of N-Sulfonyl Pyridinium Salts for Novel Organic Synthesis. University of Virginia, Chemistry - Graduate School of Arts and Sciences, PHD (Doctor of Philosophy), 2023-11-09, https://doi.org/10.18130/t89k-3916.
