Synthesis, structure, and stereodynamics of an N,N-chiral 'proton sponge'

European Journal of Organic Chemistry

Volumn , Issue 10, 1999, Pages 2501-2510

  Charmant, Jonathan P H ^a   Lloyd Jones, Guy C ^a   Peakman, Torren M ^a   Woodward, Robert L ^a  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

Author keywords

Isotopic labelling; N Chirality; NMR; Proton Sponges; Stereodynamics

Indexed keywords

NAPHTHALENE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; DIASTEREOISOMER; DIELECTRIC CONSTANT; DIPOLE; ENTHALPY; ENTROPY; MOLECULAR MODEL; MOLECULAR STABILITY; SPECTRAL SENSITIVITY; STEREOCHEMISTRY; SYNTHESIS; THERMODYNAMICS;

EID: 0032840169     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (29)

1. W. G. Brown, N. J. Letang, J. Am. Chem. Soc. 1941, 63, 358-361.
2. R. W. Alder, P. S. Bowman, W. R. S. Steele, D. R. Winterman, J. Chem. Soc., Chem. Commun. 1968, 723-724.
3. Review: H. A. Staab, T. Saupe, Angew. Chem. 1988, 100, 895; Angew. Chem. Int. Ed. Engl. 1988, 27, 865-879.
4. Review: H. A. Staab, T. Saupe, Angew. Chem. 1988, 100, 895; Angew. Chem. Int. Ed. Engl. 1988, 27, 865-879.
5. H. A. Staab, C. Krieger, G. Hieber, K. Oberdorf, Angew. Chem., Int. Ed. Engl. 1997, 36, 1884-1886.
6. R. W. Alder, N. C. Goode, N. Miller, F. Hibbert, K. P. P. Hunte, H. J. Robbins, J. Chem. Soc., Chem. Commun. 1978, 89-90.
7. F. Hibbert, S. Phillips, J. Chem. Research (S) 1990, 90-91 and references therein.
8. Review: A. F. Pozharskii, Russ. Chem Rev. 1998, 67, 1-24.
9. Part of this work has appeared in communication form: J. P. H. Charmant, G. C. Lloyd-Jones, T. M. Peakman, R. L. Woodward, Tetrahedron Lett. 1998, 39, 4733-4736.
10. + is stereolabile at ambient temperature - see references [8] and [11].
11. + see: J. A. Gerlt, M. M. Kreevoy, W. W Cleland, P. A. Frey, Chemistry &p̄ Biology 1997, 4, 259-267; J. P. Guthrie, Chemistry & Biology 1996, 3, 163-170; G. H. Barnett, F. Hibbert, J. Am. Chem. Soc. 1984, 106, 2080; For leading references on asymmetric H-bonds, see: C. L. Perrin, J. B. Nielson, J. Am. Chem. Soc. 1997, 119, 12734-12741.
12. + see: J. A. Gerlt, M. M. Kreevoy, W. W Cleland, P. A. Frey, Chemistry &p̄ Biology 1997, 4, 259-267; J. P. Guthrie, Chemistry & Biology 1996, 3, 163-170; G. H. Barnett, F. Hibbert, J. Am. Chem. Soc. 1984, 106, 2080; For leading references on asymmetric H-bonds, see: C. L. Perrin, J. B. Nielson, J. Am. Chem. Soc. 1997, 119, 12734-12741.
13. + see: J. A. Gerlt, M. M. Kreevoy, W. W Cleland, P. A. Frey, Chemistry &p̄ Biology 1997, 4, 259-267; J. P. Guthrie, Chemistry & Biology 1996, 3, 163-170; G. H. Barnett, F. Hibbert, J. Am. Chem. Soc. 1984, 106, 2080; For leading references on asymmetric H-bonds, see: C. L. Perrin, J. B. Nielson, J. Am. Chem. Soc. 1997, 119, 12734-12741.
14. + see: J. A. Gerlt, M. M. Kreevoy, W. W Cleland, P. A. Frey, Chemistry &p̄ Biology 1997, 4, 259-267; J. P. Guthrie, Chemistry & Biology 1996, 3, 163-170; G. H. Barnett, F. Hibbert, J. Am. Chem. Soc. 1984, 106, 2080; For leading references on asymmetric H-bonds, see: C. L. Perrin, J. B. Nielson, J. Am. Chem. Soc. 1997, 119, 12734-12741.
15. -, in full, elsewhere: G. C. Lloyd-Jones, P. Hodgson, M. Murray, T. M. Peakman, R. L. Woodward, Chem. Eur. J., manuscript in preparation.
16. G. Bar-Haim, R. Shach, M. Kol, Chem. Commun. 1997, 229-230; G. Bar-Haim, M. Kol, J. Org. Chem. 1997, 62, 6682-6683.
17. G. Bar-Haim, R. Shach, M. Kol, Chem. Commun. 1997, 229-230; G. Bar-Haim, M. Kol, J. Org. Chem. 1997, 62, 6682-6683.
18. 4, is probably required to effect the second alkylation. The NaH/dialkyl sulphate method has been used extensively. Selective trialkylation of 1,8-diaminona-phathalenes with alkyl iodides has also been reported by Pozharskii et al. - see reference [7].
19. + and 1. However, the measurement was complicated by a side reaction that resulted in extensive debenzylation. This reaction will be reported, in full, eleswhere.
20. The assignment was subsequently confirmed by low temperature dissolution - see reference [11].
21. E. L. Eliel., S. H. Wilen, L. N. Mander, The Stereochemistry of Organic Compounds, John Wiley and Sons, Chichester, UK, 1994.
22. For a dicussion of systematic errors and inaccuracies in DNMR see, for example, H. Günther, in NMR spectroscopy, Second edition, John Wiley and Sons, Chichester, UK, 1995; J. Sandström, Dynamic NMR Spectroscopy, Academic Press, London, 1982.
23. For a dicussion of systematic errors and inaccuracies in DNMR see, for example, H. Günther, in NMR spectroscopy, Second edition, John Wiley and Sons, Chichester, UK, 1995; J. Sandström, Dynamic NMR Spectroscopy, Academic Press, London, 1982.
24. In effect it must interconvert object and mirror image, a so-called narcisistic process.
25. -1 - see R. W. Alder, J. E. Anderson, J. Chem. Soc., Perkin Trans 2 1973, 2086-2088).
26. R. W. Alder, M. R. Bryce, N. C. Goode, N. Miller, J. Owen, J. Chem. Soc., Perkin Trans. 1 1981, 2840-2847.
27. G. H. Coleman, C. R. Hauser, J. Am. Chem. Soc. 1928, 50, 1196.
28. M. L. Kaplan, F. A. Bovey, H. N. Cheng, Anal. Chem. 1975, 47, 1703-1704; A. L. Van Geet, Anal. Chem. 1970, 42, 679-680
29. M. L. Kaplan, F. A. Bovey, H. N. Cheng, Anal. Chem. 1975, 47, 1703-1704; A. L. Van Geet, Anal. Chem. 1970, 42, 679-680