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Dr R. Michael Paton

Dr R. Michael Paton

Honorary Fellow in Chemistry

Room 108

University of Edinburgh
Joseph Black Building
David Brewster Road
Edinburgh
EH9 3FJ

Research Interests

Organic synthesis, heterocyclic chemistry, carbohydrate synthesis, reactive intermediates, organic polymer chemistry.

Research Overview

The main theme of our research is studying the chemistry of 1,3-dipoles and their synthetic applications. Recent highlights include:

  • The generation and cycloaddition reactions of nitrile sulfides, a rare class of short-lived nitrilium betaines, and their use for the synthesis of five-membered heterocycles incorporating the C=N-S unit, eg isothiazoles and 1,2,4-thiadiazoles;
  • Establishing an efficient route to pyranosyl nitrile oxides and their use for the synthesis of novel C-glycosides, eg pyranosyl perimidines and various pyranosyl benzazoles.
  • Nitrile oxide chemistry has also been used for the synthesis of pseudodisaccharides, carbohydrate-funtionalised polymers (neoglycopolymers) and higher carbon monosaccharides.

Other research interests include: chemical modification of vegetable oils, functionalisation of polyketones (CO-alkene alternating copolymers), and the chemistry of cellulose-derived levoglucosenone.

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Publications

  1. Smellie, I.A.S.; Moggach , S.A. ; Paton, R.M., Synthesis of novel amidoxime-linked pseudo-disaccharides, Tetrahedron Lett., 2011, 52, 95-97.
  2. Smellie, I.A.S.; Fromm, A.; Moggach , S.A. ; Paton, R.M., Synthesis and structure of 2-pyranosylperimidines, Carbohydr. Res., 2011, 346, 43-49.
  3. Smellie, I.A.S.; Fromm, A,; Fabianni, F.; Oswald, I.D.H.; White, F.J.; Paton, R.M., Synthesis of 2-pyranosyl benzothiazoles, benzimidazoles and benzoxazoles via nucleophilic addition reactions of pyranosyl nitrile oxides, Tetrahedron, 2010, 66, 7155-7160.
  4. Fordyce, E.A.F.; Morrison, A.J.; Sharpe, R.D.; Paton, R.M., Microwave-induced generation and reactions of nitrile sulfides: an improved method for the synthesis of isothiazoles and 1,2,4-thiadiazoles, Tetrahedron, 2010, 66, 7192-7197.
  5. Mitchell, W.R.; Paton, R.M., Flash vacuum pyrolysis of 1,2,5-oxadiazole 2-oxides and 1,2,3-triazole 1-oxides, Arkivoc, 2010, (x), 34-54.
  6. Murphy, J.J.; Furusho, H.; Paton, R.M.; Nomura, K., Precise synthesis of poly(macromonomer)s containing sugars by repetitive ROMP and their attachments to poly(ethylene glycol): synthesis, TEM analysis and their properties as amphiphilic block fragments, Chem. Eur. J, 2007, 13, 8985-8997.