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An Investigation on the Synthesis of New Molecular Architectures from the Cyclotrimerisation of exo- and endo-Benzotricyclo[4.2.1.02,5]nonene

✍ Scribed by Arif Dastan; Eren Uzundumlu; Metin Balci; Fabrizio Fabris; Ottorino De Lucchi

Publisher: John Wiley and Sons
Year: 2004
Tongue: English
Weight: 210 KB
Volume: 2004
Category: Article
ISSN: 1434-193X
DOI: 10.1002/ejoc.200300478

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✦ Synopsis

Abstract

We have performed an investigation on the cyclotrimerisation of molecules having exo‐ and endo‐benzotricyclo[4.2.1.0^2,5^]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. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

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