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Publications


2004
"Synthesis and Properties of Atropisomeric Phosphinous Acids", P. Wyatt, P. Hooper and F. Sternfeld, Tetrahedron, 2004, 60, 4549-4558.

This full paper describes work done entirely by PhD student Peter Hooper.  Francine Sternfeld is the industrial supervisor at Merck.  This issue of Tetrahedron is dedicated to atropisomerism and our paper includes colour plates to graphically illustrate two similar sets of compounds that interconvert at very diffent rates.  The subtle symmetry aspects at play in this work are beautifully illustrated by the NMR spectra. 

“Light-sensitive microemulsions”, J. Eastoe, M. Sanchez-Domingez, H. Cumber, P. Wyatt and R. K. Heenan, Langmuir, 2004, 20, 1120-1125
  
“Two routes to (11,12)-dihydrodibenzo[c,g][1,2]dithiocine”, P. Wyatt and A. Hudson, Organic and Biomolecular Chemistry, 2004, 2, 1528-1530.

“UV Causes Dramatic Changes in Aggregation with Mixtures of Photoactive and Inert Surfactants”, J. Eastoe, M. Sanchez-Domingez, P. Wyatt, A. J. Orr-Ewing and R. K. Heenan, Langmuir, 2004, 20, 6120-6126.

“A photo-responsive organogel”, J. Eastoe, M. Sanchez-Domingez, P. Wyatt and R. K. Heenan, Chemical Communications, 2004, 2608-2609.
2000-2003
"Photoresponsive Microemulsions", J. Eastoe, M. Sanchez-Domingez, H. Cumber, G. Burnett, P. Wyatt and R. K. Heenan, Langmuir, 2003, 19, 6579-6581
    

‘Synthesis of racemic and enantiomerically pure (R*,R*,R*)-Tris (alpha-methylbenzyl)phosphane.  X-Ray crystal structures of the phosphane oxides and borane complexes’, P. Wyatt, H. Eley, J. Charmant, B. J. Daniel and A. Kantacha, Eur. J. Org. Chem., 2003, 4216-4226

All of the synthetic work described in this full paper was conducted by PhD student Helen Eley.  The other authors concerned crystallographic aspects of the molecules.  Phosphines of this kind are in a rapidly developing area of chemistry.  We have reached this particularly attractive target before the large American groups in this area.  The phosphine was especially difficult to make and many of our attempts failed.  The failed routes are detailed in the paper which makes the success all the sweeter and a testament to the skill and tenacity of the research student.  This paper attracted the comment 'this paper provides an important lesson in stereochemistry' from one of the referees.

"Properties of a Stilbene-Containing Gemini Photosurfactant:  Light-Triggered Changes in Surface Tension and Aggregation", J. Eastoe, M. Sanchez-Domingez, P. Wyatt, A. Beeby and R. K. Heenan, Langmuir, 2002, 18, 7837-7844

FRONT COVER PAPER.   The strikingly visual nature of this work (light causes an obvious change in droplet shape) helped us gain the front cover of Langmuir. 
 
"Synthesis, X-ray structures and chemistry of enantiomerically pure10,11-dihydro-5-phenyl-5H-dibenzo[b,f]phosphepine 5-oxides", P. Wyatt, S. Warren, M. McPartlin and T. Woodroffe, J. Chem. Soc., Perkin Trans. 1, 2001, 279-297.

The paper is peppered with illustrations of interesting spectra including variable temperature work and the X-ray structures illustrate the different ring conformations possible. 

“Separation of diol enantiomers — a remarkable influence of water’ P. Wyatt, Tetrahedron: Asymmetry, 2001, 12, 3329-3331. 

This communication provides a graphic illustration of how a chiral HPLC – a technique that is used routinely globally can give wildly different results.  This paper shows that this difference is down to the small water content in one of the solvents (water makes it work).
"Synthesis of the novel amine (R*,R*,R*)-tris-(alpha-methylbenzyl)amine.  X-Ray crystal structures of racemic and enantiomerically pure forms", P. Wyatt, C. P. Butts, V. Patel and B. Voysey, J. Chem. Soc., Perkin Trans. 1, 2000, 4222-4223. 

This communication describes work carried out by one PhD student, Ben Voysey.  Vipulkumar Patel was the industrial supervisor from Glaxo. 


1995-1999

“Alane – A Chemoselective Way to Reduce Phosphine Oxides”, A. Bootle-Wilbraham, S. Head, J. Longstaff and P. Wyatt, Tetrahedron Lett., 1999, 40, 5267-5270.
All of the practical workers on this paper were undergraduates.

“An efficient protocol for Sharpless-style racemic dihydroxylation”, J. Eames, H. J. Mitchell, A. Nelson, P. O’Brien, S. Warren and P. Wyatt, J. Chem. Soc., Perkin Trans. 1, 1999, 1095-1103.
   
“Studies on a Chiral (N,P) Ligand Containing a C2-Symmetric Aziridine Unit”, D. Tanner, P. Wyatt, F. Johansson, S. K. Bertilsson and P. G. Andersson, Acta Chem. Scand., 1999, 53, 263-268.

“Synthesis of Novel C2 Symmetrical and Enantiomerically Pure Thiepines”, A. Hudson, A. G. Orpen, H. Phetmung and P. Wyatt, Tetrahedron Lett., 1999, 40, 813-816. 

This communication describes synthetic work conducted entirely by PhD student Andrew Hudson.

“Alane — A Novel Way to Reduce Phosphine Oxides”, S. Griffin, L. Heath and P. Wyatt, Tetrahedron Lett., 1998, 39, 4405-4406. 

This communication describes work done by the two undergraduates Sara Griffin and Lucy Heath.  The reduction of phosphine oxides to phosphines is an important reaction and the fact that the work was achieved by undergraduates is a testament both to their skill and the robust nature of this reaction. 

“Synthesis and Chemistry of 10,11-Dihydro-5-phenyl-5H-dibenzo[b,f]phosphepin 5-Oxide, the 5-Propyl Analogue and Related Phosphonium Salts”, S. Warren and P. Wyatt, J. Chem. Soc., Perkin Trans. 1, 1998, 249-255.

“The X-ray crystal structure, conformation and preparation of anti-3,3,6,6-tetramethylthiepane-4,5-diol: stereochemistry of reduction of a heterocyclic a-hydroxy ketone”, N. Feeder, M. Ginnelly, R. V. H. Jone, S. O’Sullivan, S. Warren and P. Wyatt, J. Chem. Soc., Perkin Trans. 1, 1997, 3479-3483.

“Cyclobutanone as an electrophile for lithiated phosphine oxides: ‘internal quench’ conditions”, C. Guéguen, P. O’Brien, S. Warren and P. Wyatt, J. Organomet. Chem., 1997, 529, 279-283

“Synthesis of Achiral and Homochiral Dibenzo[b,f]phosphepin 5-Oxides Using Bromine/Lithium Exchange.  X-Ray Structure of (10R, 11R)-10,11-Dihydroxy-10,11-dihydro-5-phenyl-5H-dibenzo[b,f]phosphepin 5-Oxide”, S. Warren, P. Wyatt, M. McPartlin and T. Woodroffe, Tetrahedron Lett., 1996, 37, 5609-5612.

“Synthesis of Homochiral Dibenzo[b,f]phosphepin 5-Oxides Using a Double Ortho-lithiation Strategy ”, S. Warren and P. Wyatt, Tetrahedron: Asymmetry, 1996, 7, 989-992. 

“Asymmetric Catalysis via Chiral Aziridines”, , D. Tanner, A. Harden. F. Johansson, P. Wyatt and P. Andersson, Acta Chem. Scand., 1996, 50, 361-368.

“An Efficient Protocol for a Sharpless Style Racemic Dihydroxylation”, J. Eames, H. J. Mitchell, A. Nelson, P. O’Brien, S. Warren and P. Wyatt, Tetrahedron Lett., 1995, 36, 1719.