Thesis-2004-Blanc.pdf (3.99 MB)

New reagents for asymmetric electrophilic nitrogen transfer

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thesis
posted on 25.07.2018 by Sylvain Blanc
This thesis describes the synthesis of new chiral NH oxaziridines and their uses for electrophilic amination reactions. The introduction highlights some of the most successful electrophilic amination reagents and development of systems for the formation of carbon-nitrogen bonds. Examples of the use of camphor and fenchone NH-oxaziridines synthesized by our group are provided towards the end of the first chapter. The second chapter is dedicated to our efforts to synthesize new chiral NH-oxaziridines derived from camphor. The first part of this chapter describes the formation of 3-mono- and 3,3-disubstituted camphor nitrimine precursors. The synthesis of 3-alkyl-camphor nitrimines and their attempted conversion to oxaziridines are reported in section 2.2. Section 2.3 concerns the synthesis of 3-halo-camphor oxaziridines, and the section 2.4 attempts to synthesize 3,3-dihalo-camphor oxaziridines. Investigation of the process of ammonolysis of camphor nitrimine using ammonia is discussed in section 2.5. Section 2.6 is dedicated to the attempted formation of 3,3-diacetal camphor nitrimines. [Continues.]

History

School

  • Science

Department

  • Chemistry

Publisher

© Sylvain Blanc

Publisher 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

2004

Notes

A Doctoral Thesis. Submitted in partial fulfilment of the requirements for the award of Doctor of Philosophy at Loughborough University.

Language

en

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