Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 15, Issue 21, Pages 5289-5300Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200802548
Keywords
cyclotrimerization; density functional calculations; macrocycles; reaction mechanisms rhodium
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Funding
- Spanish MEC [CTQ2005-04968-C02-02/BQU, CTQ2005-08797-C02-01/BQU, CTQ2008-03077/BQU, CTQ2008-05409-C02-02/BQU, CTQ2006-01080]
- Catalan DURSI [2005SGR-00238, 2005SCR-00305]
- Centre de Supcrcomputacio de Catalunya (CESCA)
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A new series of 20- and 25-membered polyacetylenic azamacrocycles have been satisfactorily prepared and completely characterised by spectroscopic methods. Various [2+2+2] cyclotrimerisation processes catalysed by the Wilkinson's catalyst, [RhCl-(PPh3)(3)], were tested in the above-mentioned macrocycles. The 25-membered azamacrocycle (like the previously synthesised 15-membered azamacrocyle) led to the expected cyclotrimerised compound in contrast to the 20-membered macrocycle, which is characterised by its lack of reactivity. The difference in reactivity of the 15-, 20- and 25-membered macrocycles has been rationalised through density functional theory calculations.
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