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Preparation of Cyclophanes by Room-Temperature Ring-Closing Alkyne Metathesis with Imidazolin-2-iminato Tungsten Alkylidyne Complexes

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journal contribution
posted on 06.03.2008, 00:00 by Stephan Beer, Kai Brandhorst, Jörg Grunenberg, Cristian G. Hrib, Peter G. Jones, Matthias Tamm
Room-temperature ring-closing alkyne metathesis of 1,2-, 1,3-, and 1,4-bis(3-pentynyloxymethyl)benzenes has been investigated in the presence of catalytic amounts of an imidazolin-2-iminato tungsten alkylidyne complex. The m- and p-diynes selectively form the respective [10]metacyclophane or [10.10]paracyclophane, respectively, whereas a mixture of monomeric and dimeric cycloalkynes is obtained in the case of the o-diyne. DFT calculations reveal that the different selectivities can be attributed to the relative thermodynamic stability of the emerging cyclophanes.