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Sodium template synthesis of a 54-membered bis(pyridine) macrocycle

DOI: 10.1016/j.tetlet.2015.05.110 DOI Help

Authors: Thibault Troadec (University of Warwick) , Amber Thompson (University of Oxford) , Adrian B. Chaplin (University of Warwick)
Co-authored by industrial partner: No

Type: Journal Paper
Journal: Tetrahedron Letters , VOL 56 (31) , PAGES 4613–4615

State: Published (Approved)
Published: June 2015
Diamond Proposal Number(s): 9981

Abstract: An operationally simple and high yielding sodium-template-based synthesis of a large bis(pyridine)-based macrocycle is described. Complexation of two equivalents of 2,6-bis(10-undecen-1-oxymethyl)pyridine with Na[BArF4] (ArF = 3,5-C6H3(CF3)2) enabled the selective cross-metathesis of the terminal alkene substituents and formation of the corresponding bis(pyridine) macrocycle in 51% isolated yield. The new 54-membered macrocycle was characterised in the solid-state by X-ray diffraction in addition to verification of the structure in solution by NMR spectroscopy and ESI-MS.

Journal Keywords: Metal-Template; Sodium; Macrocycle; Olefin Metathesis

Subject Areas: Chemistry

Instruments: I19-Small Molecule Single Crystal Diffraction

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