Acenaphane derivatives from furan macrocycles

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

Research output: Contribution to journalArticle

12 Citations (Scopus)

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
Pages (from-to)9113-9124
Number of pages12
JournalTetrahedron
Volume50
Issue number30
DOIs
StatePublished - Jan 1 1994
Externally publishedYes

Fingerprint

Molecular recognition
Xylenes
Stereochemistry
X ray analysis
Isomers
Nuclear magnetic resonance spectroscopy
X-Rays
Single crystals
Derivatives
X rays
Magnetic Resonance Spectroscopy
furan
macrocycle 1
4-xylene
Proton Magnetic Resonance Spectroscopy

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

H. Kohnke, F., F. Parisi, 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

Acenaphane derivatives from furan macrocycles. / H. Kohnke, Franz; F. Parisi, Melchiorre; Raymo, Francisco; A. O'Neil, Paul; J. Williams, David.

In: Tetrahedron, Vol. 50, No. 30, 01.01.1994, p. 9113-9124.

Research output: Contribution to journalArticle

H. Kohnke, F, F. Parisi, M, Raymo, F, A. O'Neil, P & J. Williams, D 1994, 'Acenaphane derivatives from furan macrocycles', Tetrahedron, vol. 50, no. 30, pp. 9113-9124. https://doi.org/10.1016/S0040-4020(01)85377-1
H. Kohnke F, F. Parisi M, Raymo F, A. O'Neil P, J. Williams D. Acenaphane derivatives from furan macrocycles. Tetrahedron. 1994 Jan 1;50(30):9113-9124. https://doi.org/10.1016/S0040-4020(01)85377-1
H. Kohnke, Franz ; F. Parisi, Melchiorre ; Raymo, Francisco ; A. O'Neil, Paul ; J. Williams, David. / Acenaphane derivatives from furan macrocycles. In: Tetrahedron. 1994 ; Vol. 50, No. 30. pp. 9113-9124.
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