Metal-templated macrocycle synthesis in an ionic liquid: A comparison with reaction in protic solvents

Jie Zhang, Shi Xia Luo, Adam McCluskey, Geoffrey A. Lawrance

Research output: Contribution to journalArticleResearchpeer-review

4 Citations (Scopus)

Abstract

Metal-directed macrocyclization reactions of [Cu(diamine)2] 2+ (diamine = ethane-, propane-, and trans-cyclohexane-1,2-diamine, and propane-1,3-diamine) and [Co(ethane-1,2-diamine)3]3+ with formaldehyde and a nitroalkane carbon acid were examined for the first time in an ionic liquid solvent (1-butyl-3-methylimidazolium tetrafluoroborate), and compared with outcomes in molecular solvents. Products were identical and overall yields similar in ionic liquid and protic solvents. However, two important advantages were defined with the ionic liquid solvent: first, macrocycles form almost exclusively, rather than the mixture of macrocyclic and acyclic products formed in protic solvents; second, larger ring (16- vs. 14-membered) macrocycles form in much higher yield in ionic liquid.

Original languageEnglish
Pages (from-to)1-5
Number of pages5
JournalSynthesis and Reactivity in Inorganic, Metal Organic, and Nano Metal Chemistry
Volume43
Issue number1
DOIs
Publication statusPublished - 2013
Externally publishedYes

Keywords

  • Cobalt(III)
  • Copper(II)
  • Ionic liquid
  • Template synthesis
  • Tetraaza macrocycle

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