Troadec, Thibault, Thompson, Amber L. and Chaplin, Adrian B. (2015) Sodium template synthesis of a 54-membered bis(pyridine) macrocycle. Tetrahedron Letters, 56 (31). pp. 4613-4615. doi:10.1016/j.tetlet.2015.05.110 ISSN 0040-4039.

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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 characterized in the solid-state by X-ray diffraction in addition to verification of the structure in solution by NMR spectroscopy and ESI-MS.

Item Type:	Journal Article
Divisions:	Faculty of Science, Engineering and Medicine > Science > Chemistry
Journal or Publication Title:	Tetrahedron Letters
Publisher:	Elsevier
ISSN:	0040-4039
Official Date:	29 July 2015
Dates:	Date Event 29 July 2015 Published 3 June 2015 Available 29 May 2015 Accepted 1 May 2015 Submitted
Volume:	56
Number:	31
Page Range:	pp. 4613-4615
DOI:	10.1016/j.tetlet.2015.05.110
Status:	Peer Reviewed
Publication Status:	Published
Access rights to Published version:	Restricted or Subscription Access
Date of first compliant deposit:	28 May 2016
Date of first compliant Open Access:	30 June 2016

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