o-Fluoranil chemistry: Diels-Alder versus hetero-Diels-Alder cycloaddition.
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.
Lemal
David M
DM
Department of Chemistry, Dartmouth College, Hanover, New Hampshire 03755, USA. david.m.lemal@dartmouth.edu
Ramanathan
Sudharsanam
S
Shellito
John
J