Publication Details (including relevant citation information):
Rose, Brad D., Reiter, Richard C., Stevenson, Cheryl D., Angewandte Chemie International Edition, 2008, 47 (45), 8714-8718
Annulyne not like benzyne: The base-initiated condensation of hexadiyne in nonpolar solvents leads directly to the symmetrical isomers of annulyne, i.e. the all cis isomer, which exists as its cumulene, and the 6,9-trans,trans isomer. One-electron transfer to this mixture leads to the formation of an unsymmetrical annulyne radical anion, which transfers an electron to the all cis system leading to the biphenyl radical anion, while reduction of the other isomer leads to heptalene (see scheme).
Address (URL): http://dx.doi.org/10.1002/anie.200803863