Unusual Tethering Effects in the Schmidt Reaction of Hydroxyalkyl Azides with Ketones: Cation-π and Steric Stabilization of a Pseudoaxial Phenyl Group was written by Katz, Christopher E.;Aube, Jeffrey. And the article was included in Journal of the American Chemical Society in 2003.Name: Ethyl 2-(4-fluorophenyl)acetate This article mentions the following:
The Lewis acid-promoted reactions of chiral 2-aryl-3-azido-1-propanols with 4-substituted cyclohexanones lead to iminium ethers and ultimately caprolactams (following a hydrolysis step). In this study, it is shown that these reactions afford variable ratios of products, depending on the electronic nature of the Ph group. These results are interpreted in the context of a cation-π stabilizing effect in the product-determining reaction intermediate. Remarkably, the best selectivity was obtained when an azidopropanol reagent containing a quaternary center was used; a control experiment showed that the high selectivity observed in this result depended upon the free rotation of the pseudoaxial aromatic group in the intermediate that affords the major product. In the experiment, the researchers used many compounds, for example, Ethyl 2-(4-fluorophenyl)acetate (cas: 587-88-2Name: Ethyl 2-(4-fluorophenyl)acetate).
Ethyl 2-(4-fluorophenyl)acetate (cas: 587-88-2) belongs to esters. Esters are widespread in nature and are widely used in industry. In nature, fats are in general triesters derived from glycerol and fatty acids. Esters are responsible for the aroma of many fruits. Liquid esters of low volatility serve as softening agents for resins and plastics. Esters also include many industrially important polymers. Polymethyl methacrylate is a glass substitute sold under the names Lucite and Plexiglas; polyethylene terephthalate is used as a film (Mylar) and as textile fibres sold as Terylene, Fortrel, and Dacron.Name: Ethyl 2-(4-fluorophenyl)acetate
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