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Paraic James
B.Sc., Ph.D. (NUI), M.I.C.I., M.R.S.C., C.Chem.
Senior Lecturer, Organic Chemistry

Name: Dr Paraic James
Phone Number: 5126
Room Number: X108
Email Address:

 

Synthesis and Structure Determination in Organic Chemistry

Our interest is in three broad areas of organic chemistry. The first is the synthesis of nitrogen heterocycles. This has included the synthesis of four, five and eight- membered heterocycles. In particular the synthesis of a range of tetrazocines by ring expansion of bicyclic systems is currently an active research goal within the group.

We have identified a methodology for making compounds containing four-nitrogen atoms within the eight-membered ring and now wish to extend this work while availing of easily obtained bicyclic five-membered nitrogen heterocycles (James and co-workers, J.Chem.Res.,(S), 1995, 438, (M) 1995, 2501). The key step involves a new reaction which we have published in preliminary form i.e. the removal of the bridge-head bond of a bicyclic system of two fused five membered rings.

We described the photochemically induced electrocyclic ring expansion of a bicyclic system {3a,6a-diaryl-hexahydropyrrolo[2,3-d]-1,2,3-triazoles], to a new eight-membered ring system {2,5,6,7-tetrahydro-1,2,35-tetrazocines}.

The second area involves an active collaboration with the School of Pharmacy in Trinity College, Dublin and involves the isolation and identification of a range of natural products. The third area is the application of nuclear magnetic resonance to the solving of structural problems in organic chemistry. This area is greatly facilitated by the availability of a recently acquired 400 MHz Bruker spectrometer.

Recent Publications

1. "Synthetic Haems as Mimics for High Valent Intermediates in Haemoprotein Catalysed Oxidations. Synthesis and Oxidation of Chloro-7,8,17,18-tetracyano-5,10,15,20 tetraphenylporphyrinatoiron (III), a Haem which Contains Strongly Electron-Withdrawing Groups in the b-Pyrrole positions", S.T. Atkinson, S.P. Brady, J.P. James and K.B. Nolan, Pure & Applied Chemistry, 67 (1995) 1109.
2. "Synthesis and Crystal Structure of a Substituted 2,5,6,7-Tetrahydro-1,2,3,5-Tetrazocine: Photochemical Transformations of Substituted Pyrrolo [2,3-d]-1,2,3-Triazoles". C. Byrne, S.M. Draper, J.P. James and C.Long, J.Chem.Soc., J.Chem.Res(M), (1995) 438.
3. "The Photochemical Transformation of Cyclic Azimines: X-Ray Crystallography Analysis of Intermediates in their Sequential Phototransformations", C. Byrne, J.P. James, C. Long and D. Wilcock. J.Chem.Soc., Chem.Commun, (1996) 945. H. "Isolation of (S)-(-)-2,3-Dihydro-2,6-dimethyl-4H-benzopyran-4-one from Roots of Leontopodium alpinu", N. Comey, I. Hook, H. Sheridan, J.Walsh and P. James, J. Nat. Prod, 60 (1997) 148
4. "Studies on the cytostatic and cytotoxic effects and mode of action of 8-nitro-7-hydroxycoumarin", D. Egan, P. James, D. Cooke and R.O'Kennedy, Cancer Letters, 118 (1997) 201.
5. "The antimicrobial saponins of Yucca Schidigera and the implications of their in vitro properties for their in vivo impact", G.F.Killeen, C.A.Madigan, C.A.Connolly, G.A.Walsh, C.A.Clark, M.J.Hynes, B.F.Timmins, P.James, D.R.Headon and R.F.Power, J. Agric., Food Chem., 46 (1998) 3178.
6. "Sesquiterpene Lactones from Leontopodium Alpinum", N. Comey, A.I. Gray, I.L.Hook, P. James and H.Sheridan, Phytochemistry, 50 (1999) 1057.