(E,E)-1,4-Distyrylbenzene and Its Bisepoxy, Bis(dihydroxy), and Bis(dichloromethylene) Derivatives

Convenient preparative methods for indirect epoxidation and dichlorocyclopropanation of the two exocyclic double bonds in (E,E)-1,4-distyrylbenzene have been proposed. The procedure for epoxidation includes conjugate electrophilic bromination of (E,E)-1,4-distyrylbenzene with N-bromosuccinimide in formic acid, followed by treatment of the addition products with alkali under conditions of phase-transfer catalysis. The procedure also applies to styrene and stilbene derivatives. Dichlorocyclopropanation of (E,E)-1,4-distyrylbenzene smoothly occurs on heating in chloroform in the presence of alkali with no phase-transfer catalyst.