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Paul Wyatt

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Research

Our research divides broadly into two areas –
1.  Asymmetric Methods
2.  Photoactive Surface Science in collaboration with Prof. Julian Eastoe

Asymmetric Synthetic Methods
We look at novel ways to prepare single enantiomers.  Although the compounds themselves may be useful it is usually the tools we develop to make them that are more important.  These tools have intriguing properties about them because of the symmetry they employ.  Although the investigation and subsequent application of some symmetry elements has been thorough and successful, the study of properties of molecules with higher symmetry has had little attention.  Our programme of research concerned with the investigation of the more exotic symmetry elements and chirality.  These include —

Centrosymmetry
work ongoing...

C3 symmetry
Image of C3 amine

We were the first group to make this optically pure C3 symmetrical amine

P. Wyatt, C. P. Butts, V. Patel and B. Voysey, J. Chem. Soc., Perkin Trans. 1, 2000, 4222-4223
C3 phosphine image


We then synthesised this C3 symmetrical phosphine

P. Wyatt, H. Eley, J. Charmant, B. J. Daniel and A. Kantacha, Eur. J. Org. Chem., 2003, 4216-4226


Atropisomerism
These 2-D TLC plates show how the compounds 1,2 and 3 interconvert (and 4, 5 and 6 do not interconvert) on the TLC timescale.  In the first case the compounds have interconverted before the TLC is turned by 90° and run for the second time to give off-diagonal spots.

TLC plate under UV

Interconverting compounds

chemdraw picture
TLC plate under UV

Non-converting compounds

Chemdraw picture


These compounds featured in the Tetrahedron Special Issue about atropisomerism –

P. Wyatt, P. Hooper and F. Sternfeld, Tetrahedron, 2004, 60, 4549-4558

Other areas of research include –

New ways to reduce phosphine oxides
This work was conducted by undergraduates who showed that not only was aluminium hydride (AlH3) excellent for reducing phosphine oxides to phosphines, it was also a highly chemoselective reagent. 

A. Bootle-Wilbraham, S. Head, J. Longstaff and P. Wyatt, Tetrahedron Lett., 1999, 40, 5267-5270


Chiral Heterocycles
A double lithiation strategy was employed as our main way to make novel sulfur containing rings.  Another novel strategy made use of a double Pummerer rearrangement to make hetereocycles containing a disulfide link. 

P. Wyatt and A. Hudson, Organic and Biomolecular Chemistry, 2004, 2, 1528-1530
A. Hudson, A. G. Orpen, H. Phetmung and P. Wyatt, Tetrahedron Lett., 1999, 40, 813-816

Photoactive Surface Science
We collaborate on projects with Prof. Julian Eastoe in Physical Chemistry investigating photo-active surfactants.  Modfiying the behaviour of a detergent with light is the cleanest, 'greenest', way to achieve that modification.  Methods have previously used other chemical agents (e.g. salts) which have their own behaviour and add to chemical consumption.  If shining light on a droplet causes it to fall then the applications are manifold (precise delivery of ink droplets for example).  This work made the front cover of Langmuir, the leading American journal on surface science.

Shining light on a droplet changes the surface tension. 

drops change shape with light


This is also very evident by the contact angle that is formed with a surface (67.5° falls to 52.5°)

surface tension falls

J. Eastoe, M. Sanchez-Domingez, P. Wyatt, A. Beeby and R. K. Heenan, Langmuir, 2002, 18, 7837-7844