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EPSRC Reference:
GR/R19632/01
Title:
Useful Synthetic Transformations of Trimethylsilyl Esters and Glycals Using Hypervalent Species
Principal Investigator:
Ramsden, Professor C
Other Investigators:
Researcher Co-Investigators:
Project Partners:
Imaging Research Solutions Ltd
Department:
Sch of Chemistry & Physics
Organisation:
Keele University
Scheme:
Standard Research (Pre-FEC)
Starts:
01 October 2001
Ends:
30 September 2004
Value (£):
57,533
EPSRC Research Topic Classifications:
Chemical Synthetic Methodology
Physical Organic Chemistry
EPSRC Industrial Sector Classifications:
Chemicals
Pharmaceuticals and Biotechnology
Related Grants:
Panel History:
Panel Date
Panel Name
Outcome
06 Dec 2000
Chemistry Single Panel Dec 2000
Deferred
Summary on Grant Application Form
Using our recent results on the mechanisms of reaction of xenon difluoride, this project will investigate new and useful reactions of (a) trimethylsilyl carboxylic esters and (b) glycals that will be of general value to discovery chemists. Important innovative aspects of the proposed work are (i) our ability to control the mechanism of the reaction of XeF2 by choice of reaction vessel, solvent and substrate derivatisation and (ii) achievement of unusual modes of reaction in high yield by formation of strong Si-F bonds and elimination of volatile CO2, Xe and Me3SiF. Mechanism of reaction and/or steric effects may also control stereochemistry. A further significant feature of our approach is the ability toincorporate short-lived [18]F into molecules at the end of a synthesis by an electrophilic mechanism. By employing our recently developed preparation of [18F]XeF2, this methodology is potentially useful for positron emission tomography (PET), which is widely used in medical diagnosis and drug research. Reaction of the esters under electrophilic conditions (XeF+) in the presence of masked nucleophiles will give useful substitution products whereas reaction of glycals under single electron transfer conditions (XeF2) will give valuable F-X (= F+ X-) addition products.
Key Findings
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Potential use in non-academic contexts
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Description
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Summary
Date Materialised
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Project URL:
Further Information:
Organisation Website:
http://www.keele.ac.uk