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

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      Publication Details (including relevant citation   information):

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


      [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).

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