ORGN 506 |
| The reductive cleavage of a series of functional groups (halide, sulfide, sulfoxide, sulfone, nitrile, epoxide) via single electron transfer using lithium and di-tert-butylbiphenyl was investigated. The scaffold (inert to reducing conditions) synthesised for this purpose also allowed the measurement of the reduction potentials and analysis of the mechanisms of reduction of these groups by cyclic voltammetry. An order of reactivity was established from the electrochemical data and also by a series of intermolecular synthetic competition experiments. A range of electrophiles (alkyl halides, enones, ketones) has been used to showcase the synthetic use of the anionic intermediates from these reactions. The knowledge gained from these experiments will potentially allow us to design complex syntheses of multi-functionalised organic compounds.
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New Reactions and Methodology, Heterocycles and Aromatics, Bioorganic Chemistry
8:00 PM-10:00 PM, Tuesday, 12 September 2006 Moscone Center -- Hall D, Poster
Division of Organic Chemistry |
