ACENAPHANE DERIVATIVES FROM FURAN MACROCYCLES

Authors
KOHNKE FH PARISI MF RAYMO FM ONEIL PA WILLIAMS DJ
Citation
Fh. Kohnke et al., ACENAPHANE DERIVATIVES FROM FURAN MACROCYCLES, Tetrahedron, 50(30), 1994, pp. 9113-9124
Citations number
42
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
50
Issue
30
Year of publication
1994
Pages
9113 - 9124
Database
ISI
SICI code
0040-4020(1994)50:30<9113:ADFFM>2.0.ZU;2-J
Abstract
The macrocycle 1 reacts with benzynes to give the Diels-Alder tetra-ad duct 11 as a single isomer in good yields. Its mode of formation has n ow been investigated and its stereochemistry confirmed by X-ray crysta llographic analysis. Benzymes react with 1 stepwise with high regio an d facial selectivity. Only the mono-adduct 2 could be aromatised to th e furanaphthaphane 17, and its conformational behaviour has been inves tigated by means of dynamic 1(H) NMR spectroscopy and by single crysta l X-ray analysis. The tetra-adduct 11 exhibits molecular recognition i n the solid state selectively entrapping p-xylene when crystallised fr om a mixture of xylenes.