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Title: Synthesis of novel symmetrical macrocycle via oxidative homocoupling of bisalkyne

A novel symmetrical macrocycle has been synthesised via oxidative homocoupling of bisalkyne, diprop-2-ynyl pyridine-2,6-dicarboxylate mediated by copper (I) iodide (CuI) and 4-dimethylaminopyridine (DMAP). The precursor compound was synthesised from 2,6-pyridine dicarbonyl dichloride and propargyl alcohol in the presence of triethylamine. The reaction mixture was stirred overnight and further purified via column chromatograpy with 76% yield. Single crystal for X-ray study was obtained by recrystallization from acetone. Subsequently, a symmetrical macrocycle was synthesised from oxidative homocoupling of precursor compound in open atmosphere. The crude product was purified by column chromatography to furnish macrocycle compound with 5% yield. Both compounds were characterised by IR, {sup 1}H and {sup 13}C NMR and mass spectral techniques. The unusual conformation of the bisalkyne and twisted conformation of designed macrocycle has influence the percentage yield. This has been studied thoroughly by X-ray crystallography and electronic structure calculations.
Authors:
;  [1]
  1. School of Chemical Sciences and Food Technology, Universiti Kebangsaan Malaysia, 43600 UKM Bangi, Selangor Darul Ehsan (Malaysia)
Publication Date:
OSTI Identifier:
22308324
Resource Type:
Journal Article
Resource Relation:
Journal Name: AIP Conference Proceedings; Journal Volume: 1614; Journal Issue: 1; Conference: 2014 UKM FST postgraduate colloquium, Selangor (Malaysia), 9-11 Apr 2014; Other Information: (c) 2014 AIP Publishing LLC; Country of input: International Atomic Energy Agency (IAEA)
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY; ACETONE; ALCOHOLS; CARBON 13; CHROMATOGRAPHY; COPPER; COPPER IODIDES; CRYSTALLOGRAPHY; ELECTRONIC STRUCTURE; HYDROGEN 1; MIXTURES; MONOCRYSTALS; NUCLEAR MAGNETIC RESONANCE; OXIDATION; PRECURSOR; PYRIDINE; RECRYSTALLIZATION; SYNTHESIS; X RADIATION; YIELDS