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Professor Hamish McNab
e-mail: h.mcnab@ed.ac.uk tel: 0131 650 4718

Research Interests: Heterocyclic chemistry, flash vacuum pyrolysis (FVP), reactive intermediates, green chemistry, dyestuffs and other novel p-systems.

The core synthetic work of the group is concerned with discovery, mechanistic elucidation and development of new synthetic methods in heterocyclic chemistry employing the technique of flash vacuum pyrolysis (FVP) (see apparatus below, and the review, reference 4). Most of these reactions are either pericyclic in nature (often involving ketene intermediates generated from derivatives of Meldrum's acid 1), or take place via free radicals. Some examples of ring systems we have studied, are shown below. Many of these are strained or have other destabilizing features such as oxidative sensitivity or antiaromaticity.

The effect of heterogeneous catalysts on FVP processes (e.g. dehydration, dehydrogenation and cyclisation reactions) is being investigated in the context of green chemistry.

A collaborative study of natural textile dyes [with Dr. A. N. Hulme and Dr. A. Quye (National Museums of Scotland)] explores application of the chemistry of conjugated systems from an historical perspective. Studies of modern dyestuff chemistry are supported by industry.

Pericyclic FVP reaction  FVP apparatus Example ring systems

Current work is supported by EPSRC and by the specialty chemicals industry, and over 200 research papers have been published. Hamish McNab was awarded the 2003 Bader Prize of the Royal Society of Chemistry 'for many distinguished contributions to flash vacuum pyrolysis, to the chemistry of Meldrum's acid and to heterocyclic chemistry'.

SELECTED RECENT PUBLICATIONS

  1. Generation and reactions of 2-(2-alkenylpyrrol-1-yl)phenoxyl and the corresponding thiophenoxyl radicals. J.I.G. Cadogan, C.M. Hewage, H.McNab, A.D. MacPherson, I.S. Nicolson, D. Reed and I.H. Sadler, Org. Biomol. Chem., 2006, 4, 2446-2451.
  2. An empirical study of the effect of the variables in a flash vacuum pyrolysis (FVP) experiment. E.F. Duffy, J.S. Foot, H. McNab and A.A. Milligan, Org. Biomol. Chem., 2004, 2, 2677-2683.
  3. The natural constituents of historical textile dyes. E.S.B. Ferreira, A.N. Hulme, H. McNab and A. Quye, Chem. Soc. Rev., 2004, 33, 329-336.
  4. Chemistry without reagents: synthetic applications of flash vacuum pyrolysis. H. McNab, Aldrichimica Acta, 2004, 37, 19-26.
  5. Synthesis and chemistry of 3-tert-butyl-1,5-diaminopyrazole. A.J. Blake, D. Clarke, R.W. Mares and H. McNab, Org Biomol. Chem., 2003, 1, 4268- 4274.
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