| EPSRC Reference: |
GR/N23851/01 |
| Title: |
STRONG ELECTROGENERATED NITROGEN ANION BASES: PREPARATION, PROPERTIES AND APPLICATIONS |
| Principal Investigator: |
Utley, Professor J |
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| Department: |
chemistry |
| Organisation: |
Queen Mary University of London |
| Scheme: |
Standard Research (Pre-FEC) |
| Starts: |
01 October 2000 |
Ends: |
30 September 2003 |
Value (£): |
84,575
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| EPSRC Research Topic Classifications: |
| Chemical Synthetic Methodology |
Physical Organic Chemistry |
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Summary on Grant Application Form |
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Strong bases may conveniently be generated by electrochemical reduction of precursors (probases) to give radical-anions (direct reduction) or anions. We intend to pursue early leads from our own work to develop novel probases based on phenazine derivatives (for nitrogen-centred radical-anions) and hindered N-halo amines and amides (for cleavage to nitrogen anions). Chiral probases will be prepared and electrochemically reduced in aprotic solvent to chiral electrogenerated bases (EGBs). Their usefulness will be assessed by desymmetrisation of suitable cyclohexanones and epoxides and thus compared with chemically produced analogues. Electrochemistry produces energetic intermediates cleanly, at low temperature and in a range of reaction conditions. Important variables include solvent, counterion and temperature. Kinetic basicities of the EGBs will be measured using cyclic voltammetry with digital simulation; kinetic measurements will also be used to measure activation energies for reaction between chiral EGBs and enantiomers of carbon acids. In addition to advancing understanding of asymmetric deprotonation we aim to promote application of EGBs. Thus, cell design will be important and we will develop the more useful reactions for user friendly operation in simple flow cells at constant current.
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Key Findings |
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Potential use in non-academic contexts |
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Impacts |
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| Description |
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Sectors submitted by the Researcher |
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This information can now be found on Gateway to Research (GtR) http://gtr.rcuk.ac.uk
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