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

Dastan, A
Uzundumlu, E
Balcı, Metin
Fabris, F
De Lucchi, O
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).


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Citation Formats
A. Dastan, E. Uzundumlu, M. Balcı, F. Fabris, and O. De Lucchi, “An investigation on the synthesis of new molecular architectures from the cyclotrimerisation of exo- and endo-benzotricyclo[,5)]nonene,” EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, pp. 183–192, 2004, Accessed: 00, 2020. [Online]. Available: