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 language | English |
|---|---|
| Pages (from-to) | 9113-9124 |
| Number of pages | 12 |
| Journal | Tetrahedron |
| Volume | 50 |
| Issue number | 30 |
| DOIs | |
| State | Published - Jan 1 1994 |
| Externally published | Yes |
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ASJC Scopus subject areas
- Biochemistry
- Organic Chemistry
- Drug Discovery
Cite this
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 journal › Article
}
TY - JOUR
T1 - Acenaphane derivatives from furan macrocycles
AU - H. Kohnke, Franz
AU - F. Parisi, Melchiorre
AU - Raymo, Francisco
AU - A. O'Neil, Paul
AU - J. Williams, David
PY - 1994/1/1
Y1 - 1994/1/1
N2 - 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.
AB - 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.
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UR - http://www.scopus.com/inward/citedby.url?scp=0028129630&partnerID=8YFLogxK
U2 - 10.1016/S0040-4020(01)85377-1
DO - 10.1016/S0040-4020(01)85377-1
M3 - Article
AN - SCOPUS:0028129630
VL - 50
SP - 9113
EP - 9124
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 30
ER -