An investigation on the synthesis of new molecular architectures from the cyclotrimerisation of exo- and endo-benzotricyclo[,5)]nonene

Dastan A., Uzundumlu E., Balci M., Fabris F., De Lucchi O.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, no.1, pp.183-192, 2004 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Publication Date: 2004
  • Doi Number: 10.1002/ejoc.200300478
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.183-192
  • Keywords: arenes, copper, cyclotrimerisation, high-temperature bromination, norbornene, HIGH-TEMPERATURE BROMINATION, EFFICIENT SYNTHESIS, 2,3-DIBROMOBENZOBARRELENE, BROMOSTANNYLALKENES, SYN
  • Middle East Technical University Affiliated: No


We have performed an investigation on the cyclotrimerisation of molecules having exo- and endo-benzotricyclo[,5)]nonene skeletons (3 and 4) with the aim of producing their respective cyclotrimers 2 that feature unusual geometries and electronic properties. Activation towards the cyclotrimerisation reaction was performed using the vic-bromostannyl vinyl derivatives and was accomplished under copper-mediated or palladium-catalysed reaction conditions. While the exo isomer 3 proved to be quite reactive and afforded variable amounts of the syn and anti cyclotrimers, the endo isomer 4 turned out to be quite resistant to cyclotrimerisation because of steric hindrance. Only dimers and acyclic trimers were obtained from reactions using this substrate. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004).