Thesis-2005-Pedersen.pdf (8.24 MB)
Amides as radical precursors in heterocyclic chemistry
thesis
posted on 2018-08-14, 11:43 authored by Jan M. PedersenIn this project the use of amides as precursors for imidoyl radicals in heterocyclic chemistry
has been developed. Amides were converted to thioamides, which function as precursors for
imidoyl radical equivalents. Also, a novel protocol for the synthesis of imidoyl selanides was
developed for the purpose of using these as imidoyl radical precursors.
The precursors were used in a study of intramolecular oxidative cyclisation of imidoyl
radicals onto electron deficient pyrroles and indoles. The imidoyl radical equivalents derived
from thioamides did not cyclise onto heteroarene double bonds. In contrast, imidoyl radicals
derived from imidoyl selanides did cyclise 6-exo onto activated heteroarenes, but yields were
generally low due mainly to competing reduction of the imidoyl radical, but also due to
adduct formation with isobutyronitrile radicals originating from the initiator. [Continues.]
Funding
Loughborough University. GlaxoSmithKline plc.
History
School
- Science
Department
- Chemistry
Publisher
© Jan Mondrup PedersenPublisher statement
This work is made available according to the conditions of the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0) licence. Full details of this licence are available at: https://creativecommons.org/licenses/by-nc-nd/4.0/Publication date
2005Notes
A Doctoral Thesis. Submitted in partial fulfilment of the requirements for the award of Doctor of Philosophy at Loughborough University.Language
- en