Research Profile

Peter Byrne

Biography

I completed my undergraduate studies in chemistry in University College Dublin in 2006, and undertook a Ph.D. in the laboratory of Prof. Declan Gilheany in UCD in 2007, funded by IRCSET.  During my Ph.D. I worked primarily on the mechanism of the Wittig reaction and on developing a novel chromatography-free method for phosphine oxide removal from reaction mixtures, but also worked on the synthesis of chiral phosphines for use in catalysis.  I obtained my Ph.D. in 2011, and continued in postdoctoral work in UCD until 2014, during which time I focused on the mechanisms of phosphonium salt & ylide hydrolysis and alcoholysis, on the synthesis of strained bicyclic amines, and on the development of the phosphine oxide removal technique for industrial application. 

In 2014, I was awarded an Alexander von Humboldt Postdoctoral Fellowship to carry out research in the laboratory of Prof. Herbert Mayr in Ludwig Maximliians Universität in Munich, Germany.  My research in LMU was concentrated on the progression of a consistent rationale for understanding reactivity in organic chemistry (applications included rationalising the reactivity of ambident nucleophiles, and the electrophilicity of vinyl cations), and on the development of a quantitative organic Lewis basicity scale.

In November 2016 I joined the Chemistry Department in University College Cork as a lecturer in organic chemistry.  My research interests include the development of novel organometallic reagents for organic synthesis and novel ligands for metal complexes, relating reactivity to stability in organic chemistry (i.e.rate-equilibrium relationships for organic reagents), and the mechanism of the Wittig reaction.

Research Interests

For descriptions of research projects, see https://byrnechemistry.wordpress.com/current-projects/

Organometallic Chemistry - Development of cross coupling and bond activation methodology using first row transition metals, novel phosphine & carbene ligands, and new substrates for oxidative addition allowing extension of cross coupling methodology to new compound types.

Synthetic Chemistry - development of tandem activating/protecting groups for regioselective glycosidation reactions.

Physical Organic Chemistry - development of rate-equilibrium relationships & quantitaitve Lewis acidity & basicity scales.  Rationalisation of regioselectivity in reactions of enolates.  The mechanism of the Wittig reaction.



Publications

Books

 YearPublication
(2012)Investigation of Reactions Involving Pentacoordinate Intermediates: The Mechanism of the Wittig Reaction.
P. A. Byrne (2012) Investigation of Reactions Involving Pentacoordinate Intermediates: The Mechanism of the Wittig Reaction. Germany: Springer.   [DOI] [Details]

Peer Reviewed Journals

 YearPublication
(2017)'Why are Vinyl Cations Sluggish Electrophiles?'
P. A. Byrne, S. Kobayashi, E.-U. Würthwein, J. Ammer, H. Mayr (2017) 'Why are Vinyl Cations Sluggish Electrophiles?'. Journal of the American Chemical Society, 139   [DOI] [CORA Link] [Details]
(2016)'Ambident Reactivity of Acetyl- and Formyl-Stabilized Phosphonium Ylides'
P. A. Byrne, K. Karaghiosoff, H. Mayr (2016) 'Ambident Reactivity of Acetyl- and Formyl-Stabilized Phosphonium Ylides'. Journal of the American Chemical Society, 138   [DOI] [CORA Link] [Details]
(2016)'The Mechanism of Phosphonium Ylide Alcoholysis and Hydrolysis: Concerted Addition of the O-H Bond Across the P=C Bond'
Byrne, PA;Gilheany, DG (2016) 'The Mechanism of Phosphonium Ylide Alcoholysis and Hydrolysis: Concerted Addition of the O-H Bond Across the P=C Bond'. Chemistry - A European Journal, 22 :9140-9154 [DOI] [CORA Link] [Details]
(2016)'Quantification of the nucleophilic reactivity of nicotine'
Byrne, PA;Kobayashi, S;Breugst, M;Laub, H;Mayr, H (2016) 'Quantification of the nucleophilic reactivity of nicotine'. Journal Of Physical Organic Chemistry, 29 :759-767 [DOI] [CORA Link] [Details]
(2015)'First ever observation of the intermediate of phosphonium salt and ylide hydrolysis: P-hydroxytetraorganophosphorane'
Byrne, PA;Ortin, Y;Gilheany, DG (2015) 'First ever observation of the intermediate of phosphonium salt and ylide hydrolysis: P-hydroxytetraorganophosphorane'. Chemical Communications, 51 :1147-1150 [DOI] [CORA Link] [Details]
(2014)'Investigations on the Operation of Stereochemical Drift in the Wittig Reaction by NMR and Variable-Temperature NMR Spectroscopy of Oxaphosphetane Intermediates and Their Quench Products'
Byrne, PA;Muldoon, J;Ortin, Y;Muller-Bunz, H;Gilheany, DG (2014) 'Investigations on the Operation of Stereochemical Drift in the Wittig Reaction by NMR and Variable-Temperature NMR Spectroscopy of Oxaphosphetane Intermediates and Their Quench Products'. European Journal of Organic Chemistry, 2014 :86-98 [DOI] [CORA Link] [Details]
(2013)'The Modern Interpretation of the Wittig Reaction Mechanism'
P. A. Byrne, D. G. Gilheany (2013) 'The Modern Interpretation of the Wittig Reaction Mechanism'. Chemical Society Reviews, 42   [DOI] [CORA Link] [Details]
(2012)'Unequivocal experimental evidence for a unified Li salt-free Wittig reaction mechanism for all phosphonium ylide types: Reactions with β-heteroatom substituted aldehydes are consistently selective for cis-oxaphosphetane derived products'
P. A. Byrne, D. G. Gilheany (2012) 'Unequivocal experimental evidence for a unified Li salt-free Wittig reaction mechanism for all phosphonium ylide types: Reactions with β-heteroatom substituted aldehydes are consistently selective for cis-oxaphosphetane derived products'. Journal of the American Chemical Society, 134   [DOI] [CORA Link] [Details]
(2012)'Anomalous Z-isomer content in Wittig reaction products from keto-stabilised ylides with ortho-heteroatom substituted benzaldehydes'
P. A. Byrne, L. J. Higham, P. McGovern, D. G. Gilheany (2012) 'Anomalous Z-isomer content in Wittig reaction products from keto-stabilised ylides with ortho-heteroatom substituted benzaldehydes'. Tetrahedron Letters, 53   [DOI] [CORA Link] [Details]
(2012)'A convenient and mild chromatography-free method for the purification of the products of Wittig and Appel reactions'
P. A. Byrne, K. V. Rajendren, J. Muldoon, D. G. Gilheany (2012) 'A convenient and mild chromatography-free method for the purification of the products of Wittig and Appel reactions'. Organic and Biomolecular Chemistry, 10 :3531-3537   [DOI] [CORA Link] [Details]

Professional Activities

Honours and Awards

 YearTitleAwarding Body
2012Springer Thesis Prize Springer
2007Hugh Ryan medal University College Dublin School of Chemistry
2007IRCSET Postgraduate Funding Irish Research Council
2014Alexander von Humboldt Postdoctoral Fellowship Alexander von Humboldt Foundation

Committees

 CommitteeFunctionFrom / To
Research & Graduate Studies Committee Committee Member/

Teaching Activities

Teaching Interests

Spectroscopic techniques, with particular application to the determination of rate constants and equilibrium constants - including NMR, IR, MS, UV-Vis (including laser flash photolysis and stopped flow techniques).

Physical Organic Chemistry

Molecular orbital symmetry (use of Walsh diagrams)

Synthetic organic chemistry

Contact details

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School of Chemistry

Scoil na Ceimic

Second Floor, Kane Building, University College Cork, T12 YN60.

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