o-Fluoranil chemistry: Diels-Alder versus hetero-Diels-Alder cycloaddition |
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Authors: | Lemal David M Ramanathan Sudharsanam Shellito John |
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Institution: | Department of Chemistry, Dartmouth College, Hanover, New Hampshire 03755, USA. david.m.lemal@dartmouth.edu |
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Abstract: | The title quinone undergoes 4 + 2] cycloadditions in two ways, Diels-Alder on the ring and hetero-Diels-Alder by attack at the oxygens. The latter mode of reaction is strongly favored thermodynamically, but there is a kinetic bias favoring the normal Diels-Alder addition that often prevails, especially with cycloaddends that are not electron-rich. |
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