CHED 509 |
| The 1950 Nobel Prize in Chemistry was presented to Otto Diels and Kurt Alder for their mutual discovery of an experimental procedure known as the Diels-Alder Reaction. One molecular probe for the Diels-Alders reaction is a class of compounds known as isobenzofurans. The goal of this research is to generate a synthesis to create symmetrical and unsymmetrical isobenzofurans. Our synthesis utilizes 2,2-diphenyl-1,3-dioxalane as starting material. A halogen-metal exchange using n-butyllithium, the addition of an aldehyde, and then finally an acid catalyzed cyclization is employed to prepare the desired isobenzofuran. To date 2 isobenzofurans have been synthesized with our new synthetic route: 1,3-diphenylisobenzofuran (1,3-DPIBF) using benzaldehyde and 1-(4-chlorophenyl)-3-phenylisobenzofuran using 4-chlorobenzaldehyde. Isobenzofurans are of great significance to chemists because of their extensive pi electron system and their use as dienes in the Diels-Alder reaction. |
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Undergraduate Research Poster Session: Organic Chemistry
11:00 AM-1:00 PM, Monday, March 26, 2007 Hyatt Regency Chicago -- Riverside Center, Poster
Division of Chemical Education |