Observation of Diastereomers of the Hydrogen-Bonded Aggregate Hub(M)3∙3CA Using 1H Nuclear Magnetic Resonance Spectroscopy When CA Is an Optically-Active Isocyanuric Acid

Journal of Organic Chemistry

Volumn 62, Issue 8, 1997, Pages 2619-2621

  Simanek, Eric E ^a   Qiao, Shuang ^a   Choi, Insung S ^a   Whitesides, George M ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000038904     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo9615460     Document Type: Note

References (19)

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2. We have adopted the M/P nomenclature to describe the cyclic arrangement of the melamine groups; see: Prelog, V.; Helmchen, G. Angew. Chem., Int. Ed. Engl. 1982, 21, 567.
3. Simanek, E. E.; Wazeer, I. M.; Mathias, J. P.; Whitesides, G. M. J. Org. Chem. 1994, 59, 4904.
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7. Elhadi, F. E.; Ollis, W. D.; Stoddard, J. F. J. Chem. Soc., Perkin Trans. II 1982, 1727.
8. Williams, D. J.; Lawton, D. Tetrahedron Lett. 1975, 2, 111.
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12. Eggers, L.; Buss, V.; Henkel, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 870.
13. Lehn et al. have described a self-assembling helicate based on Cu(II) and tethered chelates that assembles with handedness; see: Hasenknopf, B.; Lehn, J.-M.; Baum, G.; Fenske, D. Proc. Natl. Acad. Sci. U.S.A. 1996, 98, 1397 and references therein.
14. Kawamoto, T.; Hammes, B. S.; Haggerty, B.; Yap, G. P. A.; Rheingold, A. L.; Borovik, A. S. J. Am. Chem. Soc. 1996, 118, 285.
15. Mitzuni, T.; Yagi, S.; Honmaru, A.; Ogoshi, H. J. Am. Chem. Soc. 1996, 118, 5318.
16. Wittung, P.; Eriksson, M.; Lyng, R.; Nielsen, P. E.; Norden, B. J. Am. Chem. Soc. 1995, 117, 10167.
17. 3 diastereomers of 1-P (or 1-M): the slight difference in chemical shift makes their assignment difficult.
18. Nuckolls, C.; Katz, T. J.; Castellanos, L. J. Am. Chem. Soc. 1996, 118, 3767.
19. A variety of CAs have been prepared by this method; see ref 2 for examples.