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p-tert-Butylcalix[5]arene: a New Synthetic Pathway and Crystal Structure of the N,N-Dimethylformamide Complex

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Abstract

The formation of p-tert-butylcalix[5]arene by the opening ofp-tert-butyldihomooxacalix [4]arene and the addition of a monomer has beenstudied. Various facets, including the effects of bases and the nature ofthe monomer added to the p-tert-butyldihomooxacalix[4]arene, have beeninvestigated. p-tert-Butylcalix[5]arene can be prepared in yields up to30%. The structure of its 1 : 2 complex with DMF has been determinedby X-ray crystallography. Crystals are triclinic, space group P¯1, a =1428.2(3) pm, b = 1837.3(3) pm, c = 1276.1(2) pm, α = 108.98(1)°,β = 105.02(2)°, γ = 95.21(1)°, Z = 2, D c = 1.059 kg m-3,final R value = 0.087. The macrocycle adopts a cone conformation, one guestenclosed inside the cavity, the other one outside.

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References

  1. A. Ninagawa and H. Matsuda: Makromol. Chem., Rapid Commun. 3, 65 (1982).

    Google Scholar 

  2. R.D. Stewart and C.D. Gutsche: Org. Prep. Proced. Int. 25(1), 137 (1993); Chem. Abstr., 118, 233614 y (1993).

    Google Scholar 

  3. K. Iwamoto, K. Araki, and S. Shinkai: Bull. Chem. Soc. Jpn. 67, 1499 (1994).

    Google Scholar 

  4. F. Vocanson, R. Lamartine, and R. Perrin: Supramol. Chem. 4, 153 (1994).

    Google Scholar 

  5. F. Vocanson and R. Lamartine: Supramol. Chem. 7, 19 (1996).

    Google Scholar 

  6. M. Perrin and S. Lecocq: J. Incl. Phenom. 11, 171 (1991).

    Google Scholar 

  7. M. Coruzzi and G.D. Andreetti: J. Chem. Soc. Perkin Trans. 2, 1133 (1982).

    Google Scholar 

  8. R.K. Juneja, K.D. Robinson, G.W. Orr, R.H. Dubois, K.A. Belmore, J.L. Atwood, J.A. Ripmeester, and C.I. Ractcliffe: J. Incl. Phenom. 13, 93 (1992).

    Google Scholar 

  9. J.F. Gallagher, G. Ferguson, V. Böhmer, and D. Kraft: Acta. Crystallogr. C50, 73 (1994).

    Google Scholar 

  10. J.L. Atwood, R.K. Juneja, P.C. Junk, and K.D. Robinson: J. Chem. Crystallogr. 24, 573 (1994).

    Google Scholar 

  11. F. Vocanson, C. Duchamp, J.B. Regnouf de Vains, and R. Lamartine: Chromatographia 41, 204 (1995).

    Google Scholar 

  12. F. Vocanson, R. Lamartine, C. Bavoux, and M. Perrin: J. Incl. Phenom. 22, 119 (1995).

    Google Scholar 

  13. Frenz, B.A.: Structure Determination Package(Enraf-Nonius) Delft, The Netherlands (1982).

    Google Scholar 

  14. P. Main, S.J. Fiske, S.E. Hull, L. Lessinger, G. Germain, J.P. Declercq, and M.M. Woolfson: MULTAN 80. A System of Computer Programs for the Automatic Solution of Crystal Structures from X-ray Diffraction Data, Universities of York, England, and Louvain, Belgium (1980).

    Google Scholar 

  15. G.M. Sheldrick: SHELXL93, University of Göttingen, Germany (1993).

    Google Scholar 

  16. A. Ettahiri, A. Thozet, and M. Perrin: Supramol. Chem. 3, 191 (1994).

    Google Scholar 

  17. E. Dahan and S.E. Biali: J. Org. Chem. 54, 6003 (1989).

    Google Scholar 

  18. N. Ehlinger, S. Lecocq, R. Perrin, and M. Perrin: Supramol. Chem. 2, 77 (1993).

    Google Scholar 

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Authors and Affiliations

  1. Laboratoire de Chimie Industrielle, CNRS-ESA, Université, 5078, Claude Bernard Lyon I

    I. DUMAZET, F. VOCANSON & R. LAMARTINE

  2. Laboratoire de Cristallographie, CNRS-ESA 5078, Université Claude Bernard Lyon I, 43, boulevard du 11 Novembre 1918, 69622, Villeurbanne cedex, France

    N. Ehlinger, S. Lecocq & M. Perrin

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  1. I. DUMAZET
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  2. N. Ehlinger
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  3. F. VOCANSON
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  4. S. Lecocq
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  5. R. LAMARTINE
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  6. M. Perrin
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DUMAZET, I., Ehlinger, N., VOCANSON, F. et al. p-tert-Butylcalix[5]arene: a New Synthetic Pathway and Crystal Structure of the N,N-Dimethylformamide Complex. Journal of Inclusion Phenomena 29, 175–185 (1997). https://doi.org/10.1023/A:1007907525620

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  • DOI: https://doi.org/10.1023/A:1007907525620

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