The action of excess DDQ on 1,4,5,8-tetrahydro-4a,8-amethanonaphthalenes bearing a methyl group and one other substituent (cyclopropyl, methyl, phenyl) at the 9 position resulted in a peculiar oxidative rearrangement to 1-vinylnaphthalene derivatives. Two closely related mechanisms, both of which involve a 1,5-sigmatropic shift of the one-carbon bridge (Berson-Willcott rearrangement), are considered for this novel process.