Synthesis and structure of tetraols with convergent and divergent arrays of hydroxy groups

(Note: The full text of this document is currently only available in the PDF Version )

Hideki Takagi, Takashi Hayashi, Tadashi Mizutani, Hideki Masuda and Hisanobu Ogoshi


Abstract

As hydrogen-bonding hosts with a partially flexible framework, two types of tetrahydroxy compounds with respectively convergent and divergent arrays of hydroxy groups were prepared. The structures of the tetraol with a diethyleneoxy bridge (1a), and that with a m-phenylenedioxy bridge (syn-13a and anti-13b) were determined by X-ray crystallographic studies. syn-13a forms an inclusion crystal with 1,4-dioxane, one molecule of which is bound in the cleft of syn-13a and the other in the intermolecular cavity.


References

  1. (a) M. Simard, D. Su and J. D. Wuest, J. Am. Chem. Soc., 1991, 113, 4696 CrossRef; (b) J. C. MacDonald and G. M. Whitesides, Chem. Rev., 1994, 94, 2383 CrossRef CAS; (c) K. Endo, T. Ezuhara, M. Koyanagi, H. Masuda and Y. Aoyama, J. Am. Chem. Soc., 1997, 119, 499 CrossRef CAS.
  2. (a) For reviews, see, J. R. Fredericks and A. D. Hamilton, in Comprehensive Supramolecular Chemistry, ed. J. L. Atwood, J. E. Davies, D. D. MacNicol, F. Vögtle and J.-M. Lehn, Elsevier, Oxford, UK, 1996, vol. 9, pp. 565–594 Search PubMed; (b) E. E. Simanek, X. Li, I. S. Choi and G. M. Whitesides, in Comprehensive Supramolecular Chemistry, ed. J. L. Atwood, J. E. Davies, D. D. MacNicol, F. Vögtle and J.-M. Lehn, Elsevier, Oxford, UK, 1996, vol. 9, pp. 595–621 Search PubMed; (c) D. A. Bell and E. V. Anslyn, in Comprehensive Supramolecular Chemistry, ed. J. L. Atwood, J. E. Davies, D. D. MacNicol, F. Vögtle and J.-M. Lehn, Elsevier, Oxford, UK, 1996, vol. 2, pp. 439–475 Search PubMed.
  3. (a) D. Koshland, Proc. Natl. Acad. Sci. USA, 1958, 44, 98; (b) D. Koshland, J. Yankeelov and J. Thoma, Fed. Proc., 1962, 21, 1031 Search PubMed; (c) D. Koshland, J. Theor. Biol., 1962, 2, 75 CAS.
  4. Examples of allosteric hosts,see: (a) P. D. Beer and A. S. Rothin, J. Chem. Soc., Chem. Commun., 1988, 52 RSC; (b) F. Ebmeyer and J. Rebek, Jr., Angew. Chem., 1990, 102, 1191 (Angew. Chem., Int. Ed. Engl., 1990, 29, 1148) CAS; (c) H.-J. Schneider and D. Ruf, Angew. Chem., 1990, 102, 1192 CAS; Angew. Chem., Int. Ed. Engl., 1990, 29, 1159 Search PubMed; (d) R. P. Sijbesma and R. J. M. Nolte, J. Am. Chem. Soc., 1991, 113, 6695 CrossRef CAS; (e) M. Inouye, M. Ueno and T. Kitao, J. Org. Chem., 1992, 57, 1639 CrossRef CAS; (f) T. Hayashi, T. Asai, H. Hokazono and H. Ogoshi, J. Am. Chem. Soc., 1993, 115, 12210 CrossRef CAS; (g) T. Mizutani, S. Yagi, A. Honmaru and H. Ogoshi, J. Am. Chem. Soc., 1996, 118, 5318 CrossRef CAS.
  5. For a review of design of flexible molecules, see R. W. Hoffmann, Angew. Chem., Int. Ed. Engl., 1992, 31, 1124 Search PubMed.
  6. N. Morelle, J. Gharbi-Benarous, F. Acher, G. Valle, M. Crisma, C. Toniolo, R. Azerad and J.-P. Girault, J. Chem. Soc., Perkin Trans. 2, 1993, 525 RSC.
  7. For preliminary accounts of preparation and X-ray crystal structure of 1a, see T. Hayashi, H. Takagi, H. Masuda and H. Ogoshi, J. Chem. Soc., Chem. Commun., 1993, 364 Search PubMed.
  8. M. P. Mertes, J. Org. Chem., 1961, 26, 5236 CAS.
  9. J. A. Marshall, B. S. DeHoff and D. G. Cleary, J. Org. Chem., 1986, 51, 1735 CrossRef CAS.
  10. A. C. T. North, D. C. Phillips and F. S. Mathews, Acta Crystallogr., Sect. A, 1968, 24, 351 CrossRef.
  11. A. Altomare, M. C. Burla, M. Cascarano, C. Giacovazzo, A. Guagliardi and G. Polidori, J. Appl. Crystallogr., 1993, 26, 343 CrossRef.
  12. DIRDIF92: P. T. Beurskens, G. Admiraal, G. Beurskense, W. P. Bosman, S. Garcia-Granda, R. O. Goulg, J. M. M. Smits and C. Smykalla( 1992). The DIRDIF program system, Technical Report of the Crystallography Laboratory, University of Nijmegen, The Netherlands.
  13. D. Cromer and J. T. Wabber, in International Tables for X-ray Crystallography, The Kynoch Press, Birmingham, England, 1974, vol. IV, Table 2.2 A Search PubMed.
  14. teXsan: Crystal Structure Analysis Package, Molecular Structure Corporation, The Woodlands, TX, 1985 and 1992.