Synthesis and configurational analysis of phosphonate cavitands

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Paola Jacopozzi, Enrico Dalcanale, Silvia Spera, Lysander A. J. Chrisstoffels, David N. Reinhoudt, Tino Lippmann and Gerhard Mann


Abstract

Synthesis, separation and configurational analysis of phosphonated and partially phosphonated cavitands derived from resorcinarenes are described. The configuration of all diastereomers has been elucidated by their 1H, 31P NMR spectra and 13C relaxation times. In all cases the course of the bridging reaction favours the formation of the sterically more crowded stereoisomers having the P[double bond, length half m-dash]O groups oriented outward with respect to the cavity.


References

  1. T. Lippmann, E. Dalcanale and G. Mann, Tetrahedron Lett., 1994, 35, 1685 CrossRef CAS.
  2. T. Lippmann, H. Wilde, E. Dalcanale, L. Mavilla, G. Mann, U. Heyer and S. Spera, J. Org. Chem., 1995, 60, 235 CrossRef CAS.
  3. P. Laglange and J.-P. Dutasta, Tetrahedron Lett., 1995, 36, 9325 CrossRef.
  4. L. M. Tunstadt, J. A. Tucker, E. Dalcanale, J. Weiser, J. A. Bryant, J. C. Sherman, R. C. Helgeson, C. B. Knobler and D. J. Cram, J. Org. Chem., 1989, 54, 1305 CrossRef CAS.
  5. D. J. Cram, S. Karbach, H.-E. Kim, C. B. Knobler, E. F. Maverick, J. L. Ericson and R. C. Helgeson, J. Am. Chem. Soc., 1988, 110, 2229 CrossRef CAS.
  6. P. Timmermann, H. Boerrigter, W. Verboom, G. J. Van Hummel, S. Harkema and D. N. Reinhoudt, J. Inclusion Phenom. Mol. Recognit. Chem., 1994, 19, 167 CrossRef.
  7. HPLC analyses of the diastereomers of 5 and 6(LiChrospher Si 60 column). Cavitand 5(CHCl3–THF 9∶1 as eluent): isomer oooo, tR= 5.60 min; isomer iooo, tR= 3.70 min; isomer iioo, tR= 8.76 min; isomer ioio, tR= 4.22 min. Cavitand 6(CHCl3–THF 4∶1 as eluent): isomer oooo, tR= 5.58 min; isomer oooi, tR= 4.76; isomer iioo, tR= 9.90 min; isomer ioio, tR= 6.53 min.
  8. W. G. Bentrude and J. H. Margis, J. Chem. Soc., Chem. Commun., 1969, 1113 RSC.
  9. C. A. Hunter, Chem. Soc. Rev., 1994, 101 RSC.
  10. D. R. Boyd, T. A. Evans, W. B. Jennings, J. F. Malone, W. O'Sullivan and A. Smith, Chem. Commun., 1996, 2269 RSC.
  11. J. P. Dutasta, personal communication.
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