ORGN 102 |
| In the initial report on the coupling reaction of alkylcarbonyloxymethyl (ACOM) halides with phenols, it was noted that the outcome of the reaction was dependent on the nucleophilicity of the phenol and the nucleofugicity of the halide. More nucleophilic phenols tended to attack the carbonyl carbon giving acylated products, while better leaving groups and less nucleophilic phenols led to alkylated products. Recently, others have noted that steric hindrance in the phenol and in the acyl portion of the ACOM halide are necessary in order to shift the product distribution in favor of the alkylated product. Contrary to these findings, we have observed that steric hindrance plays a much smaller role in the coupling reaction than suggested by the literature. An improved synthesis of ACOM halides, as well as the effect of ACOM halide structure on the coupling reaction with acetaminophen, a model phenol, will be presented. |
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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
Sci-Mix
Division of Organic Chemistry |