Conformation and Stereodynamics of Monodioxamethylene Calix[4]arene Derivatives

Journal of Organic Chemistry

Volumn 63, Issue 12, 1998, Pages 3866-3874

  Wöhnert, Jens ^a   Brenn, Jörg ^a   Stoldt, Matthias ^a   Aleksiuk, Oleg ^b   Grynszpan, Flavio ^b   Thondorf, Iris ^a   Biali, Silvio E ^b  

^a MARTIN LUTHER UNIVERSITY HALLE WITTENBERG   (Germany)

^b HEBREW UNIVERSITY OF JERUSALEM   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0347274847     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9720602     Document Type: Article

References (41)

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2. For reviews on calixarenes see: (a) Gutsche, C. D. Calixarenes; Royal Society of Chemistry: Cambridge, 1989. (b) Calixarenes: A Versatile Class of Macrocyclic Compounds; Vicens, J., Böhmer, V., Eds., Kluwer: Dordrecht, 1991. (c) Böhmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713. (d) Gutsche, C. D. Aldrichimica Acta 1995, 28, 1.
3. For reviews on calixarenes see: (a) Gutsche, C. D. Calixarenes; Royal Society of Chemistry: Cambridge, 1989. (b) Calixarenes: A Versatile Class of Macrocyclic Compounds; Vicens, J., Böhmer, V., Eds., Kluwer: Dordrecht, 1991. (c) Böhmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713. (d) Gutsche, C. D. Aldrichimica Acta 1995, 28, 1.
4. For reviews on calixarenes see: (a) Gutsche, C. D. Calixarenes; Royal Society of Chemistry: Cambridge, 1989. (b) Calixarenes: A Versatile Class of Macrocyclic Compounds; Vicens, J., Böhmer, V., Eds., Kluwer: Dordrecht, 1991. (c) Böhmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713. (d) Gutsche, C. D. Aldrichimica Acta 1995, 28, 1.
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32. 3 the most populated conformer of 3 is the cone/BC.
33. For a review see: Perrin, C. L.; Dwyer, T. J. Chem. Rev. 1990, 90, 935. For examples of the determination of the kinetics of the interconversions of the conformers of calixarene derivatives by 2D-EXSY spectroscopy see: (a) Blixt, J.; Detellier, C. J. Am. Chem. Soc. 1994, 116, 11957. (b) van Loon, J.-D.; Groenen, L. C.; Wijmenga, S. S.; Verboom, W.; Reinhoudt, D. N.; J. Am. Chem. Soc. 1991, 113, 2378.
34. For a review see: Perrin, C. L.; Dwyer, T. J. Chem. Rev. 1990, 90, 935. For examples of the determination of the kinetics of the interconversions of the conformers of calixarene derivatives by 2D-EXSY spectroscopy see: (a) Blixt, J.; Detellier, C. J. Am. Chem. Soc. 1994, 116, 11957. (b) van Loon, J.-D.; Groenen, L. C.; Wijmenga, S. S.; Verboom, W.; Reinhoudt, D. N.; J. Am. Chem. Soc. 1991, 113, 2378.
35. For a review see: Perrin, C. L.; Dwyer, T. J. Chem. Rev. 1990, 90, 935. For examples of the determination of the kinetics of the interconversions of the conformers of calixarene derivatives by 2D-EXSY spectroscopy see: (a) Blixt, J.; Detellier, C. J. Am. Chem. Soc. 1994, 116, 11957. (b) van Loon, J.-D.; Groenen, L. C.; Wijmenga, S. S.; Verboom, W.; Reinhoudt, D. N.; J. Am. Chem. Soc. 1991, 113, 2378.
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37. ○.
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39. The intensity of the exchange cross-peaks between the two dioxamethylene signals are influenced also by the mutual NOE effects which have an opposite sign to the magnetization transfer effects due to the dynamic process. These NOE effects should not contribute significantly to the cross-peak intensities at the small mixing times used, but strictly the values obtained for the barrier represent only an upper limit.
40. Thondorf, I.; Hillig, G.; Brandt, W.; Brenn, J.; Barth, A.; Böhmer, V. J. Chem. Soc., Perkin Trans. 2 1994, 2259.
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