27370-85-0Relevant articles and documents
Photochemistry of linear-shaped phenylacetylenyl- and (phenylacetylenyl) phenylacetylenyl-substituted aromatic enediynes
Sugiyama, Yoko,Shinohara, Yoshihiro,Momotake, Atsuya,Takahashi, Kayori,Kanna, Yoko,Nishimura, Yoshinobu,Arai, Tatsuo
scheme or table, p. 10929 - 10935 (2011/02/17)
The series of linear-shaped phenylacetylenyl- and (phenylacetylenyl) phenylacetylenyl-substituted aromatic enediynes 1-3 were synthesized as pure trans and cis isomers and their photochemistry explored. With expansion of the π-electron system, the absorpt
A p-benzyne to m-benzyne conversion through a 1,2-shift of a phenyl group. Completion of the benzyne cascade
Polishchuk, Alexei L.,Bartlett, Kevin L.,Friedman, Lee A.,Jones Jr., Maitland
, p. 798 - 806 (2007/10/03)
Pyrolysis of 1,6-diphenylhexa-1,5-diyne-cis-3-ene at 800-1000 °C leads to a mixture of 1- and 2-phenylbiphenylene, along with triphenylene. Formation of the two biphenylenes is taken as strong evidence of the rearrangement of a p-benzyne into a m-benzyne through a shift of one of the phenyl groups. Copyright
An iterative approach to cis-oligodiacetylenes
Kosinski, Christoph,Hirsch, Andreas,Heinemann, Frank W.,Hampel, Frank
, p. 3879 - 3890 (2007/10/03)
Phenyl-terminated cis-oligodiacetylenes such as 18, containing a π-conjugated backbone with four triple and three double bonds, were synthesized using Pd-catalysed Sonogashira coupling reactions. Compound 18 represents the longest cis-oligoenyne system to date, but it suffers from the drawback of cis/trans isomerization observed in solution. In order to avoid cis/trans isomerization in such cis-oligodicacetylenes, the ene moieties within the oligomeric backbone were locked by incorporation into ring systems. 1,2-Dibromocyclopentene was used as an olefinic building block for this purpose, permitting the iterative synthesis of the cis-oligodiacetylenes 27 and 28, possessing the same π-conjugated backbone as 18. Unlike that compound, however, 27 and 28 are stable both in solution and in the solid state. Whereas X-ray crystallography revealed a completely planar structure for 27 in the single crystal, NMR and computational investigations suggest that a preferred helical conformation is likely in solution.