Professor R.N. Butler

National University of Ireland, Galway.

B.Sc.1964; UCC College Scholar Award. Royal Commission for 1851 Exhibition Scholarship for Ireland, 1967; Ph.D. (N.U.I.), 1967; D.Sc. (N.U.I.), 1974; Member of Royal Irish Academy (1979); Fellow of Royal Society of Chemistry; Fellow of Inst. Chem. Ireland; Member International Society of Heterocyclic Chemistry; Chair National Committee for Chemistry Royal Irish Academy 1989-1992; Chair Royal Society of Chemistry Ireland 1993-1996; President Institute of Chemistry of Ireland 1986- 1988. Fellow at University of Leicester studying applications of NMR and ESR spectroscopy 1967-1969; Principal Sligo Regional Technical College 1970-1971; Lecturer and Associate Professor at University College Galway, 1971- 1981; Professor of Chemistry at University College Galway/National University of Ireland, Galway, 1981-2008. Boyle-Higgins Gold Medal of Institute of Chemistry of Ireland 1998.

Research Interests

Cycloaddition, cyclisation and oxidation reactions with organic compounds of nitrogen, oxygen and sulphur. 1,3-Dipoles.
Reaction mechanisms and reactive intermediates
Applications of Magnetic Resonance Spectroscopy

Publications

About 195 Research and Review papers mainly in Perkin Transactions of the Royal Society of Chemistry, London, American Chemical Society Journals and Tetrahedron Letters .

Books, Monographs and Major Reviews

Lead Tetra-acetate in Synthetic Reagents, vol. III pp. 277-419, Horwood Chichester, 1977.
Mercuric Acetate, Synthetic Reagents Vol. IV, pp. 15-145 Horwood, Chichester, 1981
Tetrazoles, Comprehensive Heterocyclic Chem., Vol. 5 pp. 791-838, Pergamon, Oxford, 1984
Advances in Tetrazole Chemistry, Adv. Heterocycl. Chem., 1977, 21, 323-435
Six-membered Rings with Three Heteroatoms, Rodd’s Chemistry of Carbon Compounds Supp. to 2nd Edn., Vol. IV, Part J. Elsevier, 1995, p. 241-281.
Tetrazoles, Comprehensive Heterocyclic Chem. II, vol. 4, pp. 621-678, Pergamon, Oxford 1996.
Pentazoles, Comprehensive Heterocyclic Chem. II, vol. 4, pp. 897-904, Pergamon Oxford, 1996.
Comparative Reactions of Nitrogen Compounds with the Isoelectronic Series Mercury (II), Thallium (III) and Lead (IV) Acetates. Principles of Oxidation Reactions, Chem. Rev., 1984, 84, 249-276.
The Diazotisation of Heterocyclic Primary Amines, Chem. Rev., 1975, 75, 241-257.

Recent papers

Luke A. Burke and Richard N. Butler, Computational Investigation of Rearrangements in Huisgen Cycloadducts of Azolium N-Dicyanomethanide 1,3-Dipoles with Alkynes: A Mechanistic Panoply, J. Org. Chem. 2009, 74 (15), pp 5199–5210.

Richard N. Butler,* John M. Hanniffy, John C. Stephens, and Luke A. Burke, A Ceric Ammonium Nitrate N-Dearylation of N-p-Anisylazoles Applied to Pyrazole, Triazole, Tetrazole, and Pentazole Rings: Release of Parent Azoles. Generation of Unstable Pentazole, HN₅/N₅^-, in Solution J. Org. Chem. 2008, 73, 1354-1364
See also First Calculations of ¹⁵N−¹⁵N J Values and New Calculations of Chemical Shifts for High Nitrogen Systems: A Comment on the Long Search for HN₅ and Its Pentazole Anion.
S. Ajith Perera, Adriana Gregusova and Rodney J. Bartlett, J. Phys. Chem. A, 2009, 113, (13), pp 3197–3201.
Richard N. Butler, Anthony G. Coyne, Patrick McArdle, Lisa M. Sibley and Luke A. Burke
Uncharacteristic thione behavior in a Huisgen cycloaddition reaction: a kinetic and theoretical study,
Tetrahedron Letters 48 (2007) 6684-6687
Richard N. Butler,* Anthony G. Coyne and Eamon M. Moloney, 2007, Organic synthesis in water: 1,3-dipolar cycloaddition reactions at ambient temperature with aqueous suspensions of solid reactants, Tetrahedron Letters 48 (2007) 3501–3503
Butler, R.N., Fahy, Aoife M., Fox, Anthony, A., Stephens, John C., McArdle, P, Cunningham, D. and Ryder, A. 2006. One-Pot synthesis of fluorescent 2,5-Dihydro-1,2,3-triazine Derivatives from a Cascade Rearrangment Sequence in the Reactions of 1,2,3-Triazolium-1-aminide 1,3-dipoles with Propiolate Esters. J. Org. Chem., 71, pp. 5679-5687.
Butler, R.N., Gavin, Helena, A., Moloney, Eamon M., McArdle, Patrick, Cunningham, Desmond and Burke, L.A. 2006. Spirally twisted imidazolium iminyl ylide structures from 1,2-rearrangements in reactions of imidazolium dicyanomethanide 1,3-dipoles with maleic anhydride: new perspectives on the Boekelheide-fedoruk ring expansions. Tetrahedron Letters, 47, pp. 6107-6111.
Butler, R.N., Fahy, A.F., Fox, A., Stephens, J.C., McArdle, P, Cunningham, D, Ryder, A.G. 2006. New reactive fluorophores in the 1,2,3-triazine series. Tetrahedron Letters, 47,pp. 1721-1724.
Butler, R.N., Coyne, A.G., Cunningham, W.J., Moloney, E.M. and Burke, L.A. 2005. Water and the Huisgen Cycloaddition Reaction: A Focus on Polar Contributions to the Transition State in the Reactions of Dicyano(phthalazinium)methanide with Substituted Styrenes and Benzylidene Acetones. Helvetica Chimica Acta, vol. 88, pp. 1611-1629.
Butler, R.N., Cunningham, W.J., Coyne, A.G., Burke, L.A. 2004. The Influence of Water on the Rates of 1,3-Dipolar Cycloaddition Reactions: Trigger Points for Exponential Rate Increases in Water-Organic Solvent Mixtures. Water-Super versus Water-Normal Dipolarophiles. J. Am. Chem. Soc., vol. 126, pp. 11923-11929.
Butler, R.N., Stephens, J.C. & Hanniffy, J.M. 2004. First reversible protonation of the all-nitrogen 1-aryl pentazole ring. Tetrahedron Letters, 45, pp. 1977-1979.
Butler, R.N., Stephens, J.C. Burke, L.A. 2003. First Generation of Pentazole (HN5, Pentazolic Acid), the Final Azole, and a Zinc Pentazolate Salt in Solution: A New N-Dearylation of 1-(p-methoxyphenyl) pyrazoles, a 2-(p-methoxyphenyl) tetrazole and Application of the Methodology to 1-(p-methoxyphenyl) pentazole. Chem. Commun., pp. 1016-1017. Perspective, Chemistry in Britain, 2003 (May), 39, 19.
Butler, R.N., Cloonan, M.O., Smyth, D.M., McArdle, P. Cunningham, D. 2003. The Reaction of Unstabilised 1,3,4-Oxadiazolium-N-Methanide 1,3-Dipoles with Alkenes: N-Substituted D-2-Pyrrolines: Constrast with the 1,3,4-Thiadiazolium Analogue. ARKIVOC, Issue in Honor of Professor A. Mckervey, ARKIVOC 2003 (vii) pp244-254
Butler, R.N., Coyne, A.G. Coyne, Cunningham, W.J. Burke, L.A. 2002. Kinetic and Synthetic Influences of Water and Solvent-Free Conditions on 1,3-Dipolar Cycloaddition Reactions: The Phthalazinium and Pyridazinium Dicyanomethanide 1,3-Dipoles: Surprisingly Successful Synthetic Methods. J. Chem. Soc., Perkin Trans 2, p. 1807.
Butler, R.N., Smyth, G.M., McArdle, P. Cunningham, D. 2002. A New Tricyclic Ring and a Nitrogen-Sulfur analogue of the Tri-Pentagon bowl: Cycloaddition Reactions of the unstablised 1,3,4-thiadiazolium-3-methanide 1,3-dipole: Steric Influences on the endo-effect: Substituted Pyrrolo [2,1-b]-1,3,4-thiadiazole systems: Azolium 1,3-dipoles. J. Chem. Soc. Perkin Trans 1, p.2851.
Butler, R.N., Smyth, G.M., Cloonan, M.O., McArdle, P Cunningham, D. 2002. A New Tricyclic Ring and a Nitrogen-sulfur Analogue of the tri-pentagon bowl. Substituted 5,6,7,7a-tetrahydropyrrolo[2,1-b]-1,3,4-thiadiazoles- endo- 6,7 dicarboxyimides. Chem. Commun., p. 1950.
Butler, R.N., Burke, L.A. (Rutgers University, Camden, New Jersey) Stephens, J.S. 2001. Theoretical Characterization of the Pentazole Anion with Metal Counter Ions. Calculated and Experimental 15N Shifts of Aryldiazonium, -azide and -pentazole Systems. J. Chem. Soc. Perkin Trans. 2, p. 1679.
Butler, R.N., Coyne, A.G., Burke, L.A. (Rutgers University, Camden, New Jersey), 2001. Kinetic Profile of Phthalazinium-2-dicyanomethanide 1,3-Dipole with 2p-Dipolarophiles: U-Shaped Dipolarophilic Activity and Classic Type II Dipole Behaviour. Reaction Rates and DFT Calculations. J. Chem. Soc. Perkin Trans. 2., p. 1781.
Butler, R.N., Fox, A. 2001. Transformations of selenadiazoliumyl-N-unsubstituted methanides (ylides) to new divinyl selenide derivatives and substituted 1,3,5-selenadiazines. Organoselenium systems from azolium 1,3-dipoles. J. Chem. Soc., Perkin Trans 1, p. 394.
Butler, R.N, Coyne, A.G., McArdle, P., Cunningham, D., Burke, L.A. 2001. Regioselectivity and endo/exo selectivity in the cycloadditions of the phthalazinium dicyanomethanide 1,3-dipole with unsymmetrical alkene and alkyne dipolarophiles. Unexpected reversals of regiochemistry: a combined experimental and DFT theoretical study. J. Chem. Soc., Perkin Trans 1, p. 1391.
Butler, R.N., Wallace, L.M. 2001. endo/exo Facial selectivities in cycloaddition reactions of substituted 1,2,3-triazolium-1 methanides, unstablised 1,3-dipoles, with some alkene dipolarophiles: models for 1,2,3-triazolium-1-aminides: new tetracyclic pyrrolo[1,2-c][1,2,3]benzotriazole structures: azolium 1,3-dipoles. J. Chem. Soc., Perkin Trans 1, p. 1778.
Butler, R.N., McGinley, J.M.G., Mahon, M.F., Molloy, K.C., Ní Bhrádaigh, E.P. 2001. Diorthobenzenotetra(5c,2c-tetrazolo)[5c-(2)-2c-(6)]-cyclophane. Acta Cryst., E57, p. 195.

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