Syn-cis- (2) and anti-cis- (3) pentalene dimers are easily available b
y CuCl2-induced oxidative coupling of dilithium-pentalenediide (5). On
the other hand, NBS-bromination as well of 1,5-dihydro-pentalene (4)
as of 1,2-dihydropentalene (6) gives unstable 1-bromo-1,2-dihydropenta
lene (7), while subsequent in situ elimination with Et(3)N exclusively
leads to syn-cis-pentalene dimer 2 in moderate yields.