Donor–acceptor accelerated norbornadiene rearrangements
Abstract
The norbornadienone acetals (1) with CO2Me, CONMe2, or CHO substituents at C-2 undergo rearrangement via formal 1,3-shift to norcaradienes under very mild conditions; strong donor-acceptor acceleration of either 1,3-sigmatropic rearrangement of C–C bond homolysis is indicated.