Strongly basic medium-ring diamines which mimic gas phase behaviour in solution: 1,6-Dimethyl-1,6-diazacyclodecane

Journal of the Chemical Society, Chemical Communications

Volumn , Issue 23, 1988, Pages 1528-1530

  Alder, Roger W ^a   Eastment, Paul ^a   Hext, Nicholas M ^a   Moss, Richard E ^a   Orpen, A Guy ^a   White, Jonathan M ^a  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 37049069554     PISSN: 00224936     EISSN: None     Source Type: Journal    
DOI: 10.1039/C39880001528     Document Type: Article

References (29)

1. D. H. Aue, H. M. Webb, and M. T. Bowers, J. Am. Chem. Soc. 1973,95,2699.
2. R. Yamdagni and P. Kcbarle, ibid., 1973,95,3504.
3. D. H. Auc, H. M. Webb, and M. T. Bowers,.J. Am. Chem. Soc, 1976,98,318.
4. J. Hineand W.-S. Li,7. Org. Chem., 1975,40,1795.
5. R. W. Alder, P. S. Bowman, W. R. S. Steele, and D. R. Wintcrman, Chem. Common., 1968, 723.
6. H. A. Staab and T. Saupe, Angew. Chem., Int. Ed. Engl., 1988, 27, 865.
7. A. Albert and E. P. Serjeant, The Determination of Ionisation Constants—A Laboratory Manual,' Chapman and Hall, New York, 1984.
8. R. W. Alder, N. C. Goode. N. Miller, F. Hibbert, K. P. P. Hunte, and H. J. Robbins, J. Chem. Soc, Chem. Commun., 1978, 89.
9. L. Ruzicka, M. Kobelt, O. Hafliger. and V. Prclog, Helv. Chim. Acta, 1949, 32, 544.report a pKa value of 9.14 for azacyclodecane in 80% mcthvlcellosolvc.
10. N.L. Allinger, J. Am. Chem. Soc. 1977, 99. 8127
11. U Burkert and N. L. Allinger, 'Molecular Mechanics,' American Chemical Society. Washington, D.C. 198
12. S. Profeta and N. L. Allinger, J. Am. Chem. Soc, 1985. 107, 1907.
13. J. Dale, Acta Chem. Scand., 1973,27, 1115.
14. J. Dale, in'Topics in Stereochemistry', eds. N. L. Allinger and E. L. Eliel, Wiley, New York, 1976, vol. 9, p. 199.
15. J. Dale, hr. J. Chem., mQ, 20, 3.
16. J. D. Cox and G. Pilcher, 'Thermochemistry of Organic and Organometallic Compounds.' Academic Press, London, 1970.
17. J. B. Pedley, R. D. Naylor, and S. B. Kirby, 'Thermochemical Data of Organic Compounds,' Chapman and Hall. 1986.
18. D. Kivelson, S. Winstcin. P. Bruck, and R. L. Hansen, J. Am. Chem. Soc, 1961.83,2938.
19. S. Winstein. P. Carter, F. A. L. Anet. and A. J. R. Bourn, ibid., 1965, 87, 5247.
20. F. A. L. Anet and R. Anet, in 'Determination of Organic Structures by Physical Methods.' ed. J. J. Zuckerman, Academic Press, 1971. vol. 3, ch. 7.
21. C. A. Cj. Haasnoot, F. A. A. M. de Leeuw, and C. Altona, Tetrahedron, 1980. 36, 2783; QCPE program No. 462 (3JHH), in updated form (QCPE Bulletin. May 1987) was used.
22. S. Scheiner, J. Phys. Chem., 1982, 86, 376.
23. D. J. Saturnino. M. Yamauchi. W. R. Clayton, R. W. Nelson, and S. G. Shore, J. Am. Chem. Soc, 1975, 97, 6063.
24. R. W. Alder, A. G. Orpen, and R. B. Sessions, J. Chem. Soc, Chem. Commun., 1983, 999.
25. W. B. Schaefer and R. E. Marsh, ibid., 1984, 1555.
26. R. W. Alder. I. A. Bourne, A. G. Orpen. R. B. Sessions, J. M. White, and M. Saunders, J. Am. Chem. Soc, submitted for publication.
27. J. M. White, R. W. Alder, and A. G. Orpen. Acta CrystaJlogr., Sea. C, 1988, 44, 1467 and references therein.
28. H. Yamamoto and K. Maruoka, J. Am. Chem. Soc, 1981, 103, 4186; preliminary treatment with BunLi was found to improve significantly the regiospecificity of the cleavage in this case.
29. R. W. Alder, P. Eastment, R. E. Moss, R. B. Sessions, and M. A. Stringfellow, Tetrahedron Lett., 1982, 23, 4181.