Endo-Cavity complexation and through-the-annulus threading of large calixarenes induced by very loose alkylammonium ion pairs

Organic Letters

Volumn 12, Issue 9, 2010, Pages 2092-2095

  Gaeta, Carmine ^a   Troisi, Francesco ^a   Neri, Placido ^a  

^a UNIVERSITY OF SALERNO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77951811336     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol100578z     Document Type: Article

References (29)

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8. See Supporting Information for further details.
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12. Very recently, an example of threading through the conformationally blocked pentakis(tert -butoxycarbonylmethoxy)- p-tert -butylcalix[5]arene derivative has been reported: Gattuso, G.; Notti, A.; Parisi, M. F.; Pisagatti, I.; Amato, M. E.; Pappalardo, A.; Pappalardo, S. Chem.- Eur. J. 2010, 16, 2381
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23. +a 1b: one strongly shielded and inside the cavity (with μ, Δ, γ, β, and α protons resonating at -0.42, -0.87, -1.20, -0.88, and 0.53 ppm, respectively) and the other, at more normal values of chemical shift (with ′, Δ′, γ′, β′, and α′ protons resonating at 0.94, 1.15, 1.63, 1.88, and 2.75 ppm, respectively), outside the cavity.
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26. +a 1b, thus confirming the impressive effect produced by the ion-pairing tendency of chloride anion. As expected, similar results were also obtained by addition of appropriate amounts of bases.
27. 1H NMR studies (see Table S3 in Supporting Information).
28. For recent examples diastereoisomeric pseudorotaxanes see
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