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Towards the synthesis of functionalised macrocyclic receptors
[Thesis]. Manchester, UK: The University of Manchester; 2013.
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Abstract
A practical route to the synthesis of two new macrocyclic thio-crown ethers, 13-bromo-3,6,9-trithia-15-azabicyclo[9.3.1]pentadeca-1(15),11,13-triene, 82, and 13-bromo-3,6,9-trithia-15-azabicyclo[9.3.1]pentadeca-1(15),11,13-triene-15-oxide, 84, is described. Both macrocycles were fully characterised using elemental analysis, 1H NMR, 13C NMR, and mass spectroscopy. The solid-state structure of 82 was also determined using X-ray crystallography. During these investigations it was shown that Cs+ can be replaced by K+ as an effective template in the pivotal macrocyclisation reaction. An operationally simple route to the synthesis of 4-bromo-2,6-bis((tosyloxy)methyl)pyridine 81, the key intermediate to both macrocycles, starting from chelidamic acid 75 has also been developed which will facilitate the synthesis of other macrocycles using this scaffold. The attempted functionalisation of 82 using a Heck reaction is described.