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An interesting inclusion phenomenon with (S)-1-(hydroxydiphenylmethyl)-5-azoniaspiro[4.4]nonane bromide and (S)-1-(hydroxydiphenylmethyl)-5-azoniaspiro[4.5]decane bromide and optical resolution of binaphthyl and biphenanthyl diols by inclusion crystallization with these optically active ammonium salts

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Abstract

Recrystallization of the spiro-pyrrolidinium salts (S)-1-(hydroxydiphenyl methyl)-5-azoniaspiro[4.4]nonane bromide or (S)-1-(hydroxydiphenylmethyl)-5-azoniaspiro[4.5] decane bromide from chloroform afforded a crystalline spiro-pyrrolidinium salt including two molecules of chloroform which was determined by 'H nmr elemental analysis, and X-ray analysis. Racemic 2.2′-dihydroxy-1, 1′-binaphthyl and 10, 10′-dihydroxy-9,9′-biphenanthryl have been resolved effectively by inclusion crystallization using these chiral ammonium salts.

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References

  1. Atwood, J.L.; Davies, J.E.D.; MacNicol, D.D., Eds.; InInclusion Compounds: Academic Press; London, 1984; Vols. 1–3; University Press: Oxford, 1991; Vols. 4 and 5.

    Google Scholar 

  2. Gokel, G.W., Ed., InAdvances in Supramolecular Chemistry; JAI Press: Greenwich, CT, 1990; Vol. 1; 1992, Vol. 2.

    Google Scholar 

  3. Weber, E.; Czugler, M.:Top. Curr. Chem. 1988,149, 45; Toda, F.Top. Curr. Chem. 140,43 (1987).

    Google Scholar 

  4. Toda, F.; Mori, K.J. Chem. Soc. Chem. Commun. 1986, 1357; Toda, F.; Tanaka, K.; Mak. T.C.W.Chem. Lett. 1984, 2085.

  5. Toda, F.; Ward, D.L.; Hart, H..Tetrahedron Lett. 1981,22, 3865.

    Google Scholar 

  6. Toda, F.; Sato, A.; Tanaka, K.; Mak, T.C.W.Chem Lett. 1989, 873.

  7. MacNicol, D.D.; McKendrick, J.J.; Wilson, D.R.,Chem. Soc. Rev. 1978,7, 65.

    Google Scholar 

  8. Bishop, R.; Dance, 1.J. Chem. Soc. Chem. Commun. 1979, 992.

  9. Miki, K.; Masui, A.; Kasai, N.; Miyata, M.; Shibakami, M.; Takemoto, K.,J. Am. Chem. Soc. 1988,110, 6594.

    Google Scholar 

  10. Shi, M.; Masaki, Y.J. Chem. Research (S) 1994,250; J. Chem. Res. (M),1994, 1460.

  11. Mathre, D.J.; Jones, T.K.; Xavier, L.C.; Blacklock, T.J.; Reamer, R.A.; Mohan, J.J.; Jones, E.T.T.; Hoogesteen, K.; Baum, M.W.; Grabowski, E.J.J..J. Org. Chem. 1991,56, 751.

    Google Scholar 

  12. Toda, F.; Tanaka, K..J. Org. Chem. 1994,59, 5748.

    Google Scholar 

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Shi, M., Itoh, N., Masaki, Y. et al. An interesting inclusion phenomenon with (S)-1-(hydroxydiphenylmethyl)-5-azoniaspiro[4.4]nonane bromide and (S)-1-(hydroxydiphenylmethyl)-5-azoniaspiro[4.5]decane bromide and optical resolution of binaphthyl and biphenanthyl diols by inclusion crystallization with these optically active ammonium salts. J Chem Crystallogr 26, 445–449 (1996). https://doi.org/10.1007/BF01668302

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  • DOI: https://doi.org/10.1007/BF01668302

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