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X-ray crystal structure and1H-NMR chiral shift reagent study of a crown trimer

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Abstract

3,4,5-Trimethoxybenzyl alcohol was cyclooligomerized with a bentonite clay used as a catalyst. Results of the crystal structure analysis of the racemic (±) nonamethoxy[1,1,1]orthocyclophane trimer, C30H36O9, are described. The structure was determined by X-ray diffraction at 293 K and shown to belong to the triclinic space group P\(\bar 1\). The compound possesses a distorted crown conformation with unusual C−H...O intermolecular interactions, and with a crystal packing not observed before in other related derivatives. The racemic mixture was also discriminated in its two enantiomeric isomers, using proton NMR and Eu(III) as a chiral shift reagent.

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References

  1. Collet, A.Tetrahedron 1987,43, 5725 and references cited therein; Al-Farhan, E.; Keehn, P.M.; Stevenson, R. Eds.;Tetrahedron Lett. 1992,33, 3591. Canceill, J.; Lacombe, L.; Collet, A.J. Am. Chem. Soc. 1985,107, 6993; Cram, D.J.; Tanner, M.E.; Keipert, S.J.; Knobler, C.B.J. Am. Chem. Soc.,1993,113, 8909.

    Google Scholar 

  2. Canceill, J.; Collet, A.; Gabard, J.; Kojzyba-Hibert, F.; Lehn, J.M.Helv. Chim. Acta. 1982,65, 1894.

    Google Scholar 

  3. Cram, D.J.; Weiss, J.; Helgeson, C.; Knobler, B.; Dorigo, A.E.; Houk, K.N.J. Chem. Soc. Chem. Commun. 1988,407; Moran, C.J.R.; Ericson, J.L.; Dalcanale, Bryant, J.A.; Knobler, C.B.; Cram, D.J.J. Am. Chem. Soc. 1991,113, 5707.

  4. Bosh, J.; Canals, J.; Granados, R.Anal. Quim. 1976,72, 709.

    Google Scholar 

  5. Salmón, M.; Zavala, N.; Martínez, M.; Miranda, R.; Cruz, R.; Cárdenas, J.; Gaviño, R.; Cabrera, A.Tetrahedron Lett. 1994,35, 5797.

    Google Scholar 

  6. Caglioti, V.; Liquori, A.M.; Gallo, N.; Giglio, E.; Scrocco, M.J. Inorg. Nucl. Chem. 1958,8, 572.

    Google Scholar 

  7. Cookson, R.C.; Halton, B.; Stevens, I.D.R.J. Chem. Soc. B. 1968, 767; Anand, N.K.; Cookson, R.C.; Halton, B.; Stevens, I.D.R.J. Am. Chem. Soc. 1966,88, 370. Miller, B.; Gesner, B.D.Tetrahedron Lett. 1965, 3351.

  8. Combaut, G.; Chantraine, J.; Teste, M.; Soulier, J.J.; Glombitza, K.W.Tetrahedron Lett. 1978, 1699; Manville, J.F.; Troughton, G.E.J. Org. Chem. 1973,38, 4278.

  9. Bhagwat, V.K.; Moore, D.V.; Pyman, F.L.J. Chem. Soc. 1931, 443; Burlingson, N.E.; Ripmeesler, J.A.J. Incl. Phenom. 1984,1, 403.

  10. Hyatt, J.A.; Duesler, E.N.; Curtin, D.Y.; Paul, I.C.J. Org. Chem. 1980,45, 5074.

    Google Scholar 

  11. Birnbaum, G.I.; Klug, D.D.; Ripmeester, J.A.; Tse, J.S.Can. J. Chem. 1985,63, 3258; Cerrini, S.; Giglio, E.; Mazza, F.; Pavel, N.V.Acta Crystallogr. Sect. B 1979,35, 2605.

    Google Scholar 

  12. Collet, A.; Gabard, J.; Jacques, J.; Cesario, M.; Guilhem, J.; Pascard, C.;J. Chem. Soc. Perkin. I,1981, 1630.

  13. Nakamura, H.; Iitaka, Y.; Yumada, Y.; Takeuchi, T.; Umezawa, H.Acta Crystallogr. Sect. B 1977,33, 1260.

    Google Scholar 

  14. Desiraju, G.R.Acc. Chem. Res. 1991,24, 290; Susuki, T.; Fujii, H.; Miyashi, T.; Yamashita, Y.J. Org. Chem. 1992,57, 6744; Bock, H.; Dienelt.; Schodel, H.; Havlas, Z.J. Chem. Soc. Chem. Commum. 1993, 1792.

    Google Scholar 

  15. SHELXTL-PLUS version 4.2/360 for MSDOS, Siemens Analytical X-ray Instruments Inc. XS-crystal structure solution an XLS crystal structure refinement, Madison, WI. USA 1990.

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Salmón, M., Cabrera, A., Zavala, N. et al. X-ray crystal structure and1H-NMR chiral shift reagent study of a crown trimer. J Chem Crystallogr 25, 759–762 (1995). https://doi.org/10.1007/BF01670332

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