Novel Organophosphorus Oligomers. Synthesis and conformation of α-hydroxy phenylphosphinates

Chapter one reviews the recent progress in the synthesis of phosphonopeptides, pseudopeptides containing a phosphinic, phosphonic or phosphonamide linkage in place of an amide (peptide) linkage. It describes some of the general methods for the synthesis of these pseudopeptides; for example through couplings to the nitrogen of an α-aminophosphonic acid, or Michael addition to acrylates, as well as other methods, the scope for which are not as wide yet. It also provides a summary of the reported biological activities of this class of pseudopeptides. Chapter two contains the results and discussion for a novel method for the synthesis of α-hydroxy phenylphosphinate oligomers as well as hybrid oligomers containing α-hydroxy phenylphosphinic acid and α-amino carboxylic acids. In particular, synthesis of a series of dimeric α-hydroxy phenylphosphinates are reported. The analysis of these dimers by a combination of NMR spectroscopy, X-ray crystallography and computational methods shows intramolecular hydrogen bonding in these molecules depends on the relative configuration of the carbon and phosphorus atoms. However, although the development of the synthetic methods was successful, the separation and isolation of the diastereomers was not always possible, which hindered a more comprehensive analysis of folding patterns in these molecules. Chapter three contains the experimental procedures, preparation and spectroscopic characterisation of all the chemical compounds. Crystal data and details of crystal structures are in the Appendix.

Grantor dc:publisher.institution

University of Bradford

Year dc:date.issued

2013

Author dc:creator

• Royappa, Martin

Advisor dc:contributor.advisor

• Afarinkia, Kamyar

• Organophosphorus oligomers
• Synthesis
• α-hydroxy phenylphosphinates

Statement dc:rights

• <a rel="license" href="http://creativecommons.org/licenses/by-nc-nd/3.0/"><img alt="Creative Commons License" style="border-width:0" src="http://i.creativecommons.org/l/by-nc-nd/3.0/88x31.png" /></a><br />The University of Bradford theses are licenced under a <a rel="license" href="http://creativecommons.org/licenses/by-nc-nd/3.0/">Creative Commons Licence</a>.

Language dc:language.iso

en

Handle dc:identifier.uri

http://hdl.handle.net/10454/5748

OAI identifier oai:identifier

oai:bradscholars.brad.ac.uk:10454/5748