Premium
The Isomers of [12]Annulyne and their Reactive Relationships to Heptalene and Biphenyl
Author(s) -
Rose Brad D.,
Reiter Richard C.,
Stevenson Cheryl D.
Publication year - 2008
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200803863
Subject(s) - chemistry , biphenyl , aryne , ion , base (topology) , condensation , cumulene , electron transfer , medicinal chemistry , structural isomer , photochemistry , stereochemistry , organic chemistry , molecule , mathematical analysis , physics , mathematics , thermodynamics
[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).