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Details of Grant 

EPSRC Reference: GR/N19946/02
Title: THE CATALYTIC BIRCH REDUCTION
Principal Investigator: Donohoe, Professor T
Other Investigators:
Researcher Co-Investigators:
Project Partners:
Department: Oxford Chemistry
Organisation: University of Oxford
Scheme: Standard Research (Pre-FEC)
Starts: 01 October 2001 Ends: 31 December 2003 Value (£): 133,691
EPSRC Research Topic Classifications:
Chemical Synthetic Methodology
EPSRC Industrial Sector Classifications:
Chemicals Pharmaceuticals and Biotechnology
No relevance to Underpinning Sectors
Related Grants:
Panel History:  
Summary on Grant Application Form
This proposal aims to develop the catalytic Birch reduction of aromatic compounds. We have discovered that the Birch reduction may be performed without ammonia solvent as long as naphthalene is added to a group I metal in the THF. We will begin with electron-deficient compounds that form stable dianions and investigate methodology for partial reduction with catalytic napthalene as an electron carrier. Subsequent development of this reaction should lead to an analogous procedure for reducing less electron deficient aromatic compounds, so widening the scope of the reaction. We aim to extend this procedure beyond heterocyclic systems and onto carbocyclic aromatic compounds. The nature of both the electron carrier and the proton source will be investigated. In addition, we know that very reactive electrophiles are compatible with these reaction conditions (normally they react with ammonia) and use of these species should give us some mechanistic information and also allow us to prepare valuable organic compounds in short order. Finally, the use of a solid-phase electron carrier will be investigated and the practicality of the reaction extended.The ultimate aim of this project is to develop a powerful new methodology for the partial reduction of aromatic compounds.
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Organisation Website: http://www.ox.ac.uk