ORGN 749 |
| This highly reactive, yet little studied quinone undergoes cycloaddition with a wide variety of dienophiles either at carbon to form Diels-Alder adducts or at oxygen to yield dioxenes or dioxins. Density functional calculations indicate that the oxygen heterocycles are invariably lower in energy than the corresponding Diels-Alder adducts, often by many kcal/mol, but Diels-Alder addition is nonetheless the preferred choice of numerous dienophiles. Facile photoextrusion of the dicarbonyl bridge from Diels-Alder adducts yields fluorodienes; thus, the quinone serves as a synthon for incorporating the [-CF=CF-CF=CF-] moiety into many types of structure. |
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Combinatorial, Parallel and Process Chemistry, Heterocycles, Aromatics, New Reactions and Methodology
8:00 PM-10:00 PM, Wednesday, August 22, 2007 BCEC -- Exhibit Hall - B2, Poster
Division of Organic Chemistry |