Bradley Rose - The Isomers of [12]Annulyne and their Reactive Relationships to Heptalene and Biphenyl

Version 1

      Publication Details (including relevant citation   information):

      Rose, Brad D., Reiter, Richard C., Stevenson, Cheryl D.,   Angewandte Chemie International Edition,   2008, 47 (45), 8714-8718

      Abstract:

      [12]Annulyne not like benzyne: The   base-initiated condensation of hexadiyne in nonpolar solvents   leads directly to the symmetrical isomers of [12]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 [12]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