Acenaphane derivatives from furan macrocycles

Franz H. Kohnke, Melchiorre F. Parisi, Françisco M. Raymo, Paul A. O'Neil, David J. Williams

Research output: Contribution to journalArticle

12 Scopus citations

Abstract

The macrocycle 1 reacts with benzynes to give the Diels-Alder tetra-adduct 11 as a single isomer in good yields. Its mode of formation has now been investigated and its stereochemistry confirimed by X-ray crystallographic analysis. Benzynes react with 1 stepwise with high regio and facial selectivity. Only the mono-adduct 2 could be aromatised to the furanaphthaphane 17, and its conformational behaviour has been investigated by means of dynamic 1H NMR spectroscopy and by single crystal X-ray analysis. The tetra-adduct 11 exhibits molecular recognition in the solid state selectively entrapping p-xylene when crystallised from a mixture of xylenes.

Original languageEnglish (US)
Pages (from-to)9113-9124
Number of pages12
JournalTetrahedron
Volume50
Issue number30
DOIs
StatePublished - 1994
Externally publishedYes

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ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

H. Kohnke, F., F. Parisi, M., M. Raymo, F., A. O'Neil, P., & J. Williams, D. (1994). Acenaphane derivatives from furan macrocycles. Tetrahedron, 50(30), 9113-9124. https://doi.org/10.1016/S0040-4020(01)85377-1