title: Thermal rearrangement of 7-methylbicyclo
abstract: The gas-phase thermal rearrangement of exo-7-methylbicyclo[3.2.0]hept-2-ene yields almost exclusively 5-methylnorbornene products. Inversion (i) of configuration dominates this [1,3] sigmatropic shift although some retention (r) is also observed. Because the [1,3] migration can only occur suprafacially (s) in this geometrically constrained system, the si/sr ratio of 7 observed for the migration of C7 in exo-7-methylbicyclo[3.2.0]hept-2-ene indicates that the orbital symmetry rules are somewhat permissive for the [1,3] sigmatropic migration of carbon.
authors.affiliation: Department of Chemistry, Franklin & Marshall College, Lancaster, Pennsylvania 17604-3003, USA.
authors.initials: JD
authors.lastname: Bender
authors.initials: PA
authors.lastname: Leber
authors.initials: RR
authors.lastname: Lirio
authors.initials: RS
authors.lastname: Smith