ORGN 110 |
Ordinarily the reducing ability of hydroxide ion in water is extremely low as a result of its stabilization by hydration (~100kcal/mol). Reductions of one-electron organic oxidants by HO- have only been observed previously in aprotic organic solvents (DMSO, acetonitrile or THF). We find that reductions by HO- can be performed in water in the presence of β-cyclodextrin (CD). We report that several nitroarenes are reduced to azoxybenzenes by NaOH in water in the presence of the CD. The reduction reactions most likely involve an initial electron transfer from HO- to the nitroarenes. The enhancement of the reducing ability of the HO- in water is believed to result from decreased hydration stabilization in the presence of the CD.
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Asymmetric Reactions and Syntheses, Physical Organic Chemistry, Combinatorial Chemistry, Total Synthesis
8:00 PM-10:00 PM, Sunday, 26 March 2006 Georgia World Congress Center -- Ex. Hall B4, Poster
Division of Organic Chemistry |