Transannular O-heterocyclization of twelve and thirteen membered trienes by methoxybromination procedure

The reaction of (E,E,Z)-cyclododeca-1.5,9-triene (1) with NBS and methanol gives bicyclic tetrahydrofuran derivatives (3) and (4) as well as usual 1,2-addition products while the related reaction with (Z,E,Z)-cyclotrideca-1,5,9-triene (7) leads to the bicyclic tetrahydropyran derivative (6), in both cases like O-heterocyclization products as the result of transannular participation of a methoxy group.