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 (US) |
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Pages (from-to) | 9113-9124 |
Number of pages | 12 |
Journal | Tetrahedron |
Volume | 50 |
Issue number | 30 |
DOIs | |
State | Published - 1994 |
Externally published | Yes |
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry