ORGN 96 |
| Allylic halides can in the presence of different metals react with aldehydes to form homoallylic alcohols. In recent years the one-pot procedure (i.e. the Barbier reaction) has gained renewed interest because water can be used as a solvent thereby making the reaction more “green”. Many metals are by now known to be reactive under Barbier conditions, however the mechanism for this transformation is poorly understood. By means of a Hammett study it is possible to address the nature of the reactive species, e.g. whether the reaction pathway is radical, cationic or concerted in nature. The study includes a diverse range of metals, such as Zinc, Indium, Tin, Bismuth, and Antimony, which makes it possible also to compare the differences in reactivity between different metals. The experimental study is complemented by density functional calculations (DFT), which allows a more detailed interpretation of the obtained experimental results.
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Process R&D, Physical Organic Chemistry, Heterocycles, Aromatics, Metal-Mediated Reactions
8:00 PM-10:00 PM, Sunday, March 25, 2007 Hyatt Regency Chicago -- Riverside Center, Poster
Sci-Mix
Division of Organic Chemistry |
