Transmission of polar substituent effects in the adamantane ring system as monitored by 19F NMR

Magnetic Resonance in Chemistry

Volumn 36, Issue 3, 1998, Pages 181-195

  Adcock, William ^a   Trout, Neil A ^a  

^a FLINDERS UNIVERSITY   (Australia)

Author keywords

13C NMR; 19F NMR; Adamantyl fluorides; NMR; Polar effects; Stereoelectronic; Substituent chemical shifts

Indexed keywords

FLUORINE COMPOUNDS;

13C NMR; 19F NMR; ADAMANTANES; ADAMANTYL FLUORIDE; POLAR EFFECT; POLAR SUBSTITUENTS; RING SYSTEMS; STEREOELECTRONIC; SUBSTITUENT CHEMICAL SHIFT; SUBSTITUENT EFFECT;

CHEMICAL SHIFT;

EID: 0032346670     PISSN: 07491581     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1097-458X(199803)36:3<181::AID-OMR250>3.0.CO;2-A     Document Type: Article

References (53)

1. W. Adcock and A. N. Abeywickrema, J. Org. Chem. 47, 2957 (1982).
2. For a summary and analysis, see L. M. Stock, J. Chem. Educ. 49, 400 (1972) and references cited therein; also C. A. Grob, Angew. Chem., Int. Ed. Engl. 15, 569 (1976) and references cited therein; M. Charton, Prog. Phys. Org. Chem. 13, 119 (1981) and references cited therein; C. Hansch, A. Leo and R. W. Taft, Chem. Rev. 91, 165 (1991) and references therein.
3. For a summary and analysis, see L. M. Stock, J. Chem. Educ. 49, 400 (1972) and references cited therein; also C. A. Grob, Angew. Chem., Int. Ed. Engl. 15, 569 (1976) and references cited therein; M. Charton, Prog. Phys. Org. Chem. 13, 119 (1981) and references cited therein; C. Hansch, A. Leo and R. W. Taft, Chem. Rev. 91, 165 (1991) and references therein.
4. For a summary and analysis, see L. M. Stock, J. Chem. Educ. 49, 400 (1972) and references cited therein; also C. A. Grob, Angew. Chem., Int. Ed. Engl. 15, 569 (1976) and references cited therein; M. Charton, Prog. Phys. Org. Chem. 13, 119 (1981) and references cited therein; C. Hansch, A. Leo and R. W. Taft, Chem. Rev. 91, 165 (1991) and references therein.
5. For a summary and analysis, see L. M. Stock, J. Chem. Educ. 49, 400 (1972) and references cited therein; also C. A. Grob, Angew. Chem., Int. Ed. Engl. 15, 569 (1976) and references cited therein; M. Charton, Prog. Phys. Org. Chem. 13, 119 (1981) and references cited therein; C. Hansch, A. Leo and R. W. Taft, Chem. Rev. 91, 165 (1991) and references therein.
6. (a) C. A. Grob and R. Rich, Tetrahedron Lett. 663 (1978); C. A. Grob and R. Rich, Helv. Chim. Acta. 62, 2793 (1979);
7. (a) C. A. Grob and R. Rich, Tetrahedron Lett. 663 (1978); C. A. Grob and R. Rich, Helv. Chim. Acta. 62, 2793 (1979);
8. (b) R. Bielmann, C. A. Grob, D. Kury and Y. Guo-Wei, Helv. Chim. Acta 68, 2158 (1985).
9. W. Adcock and T. C. Khor, J. Am. Chem. Soc. 100, 7799 (1979).
10. (a) W. F. Reynolds, Prog. Phys. Org. Chem. 14, 165 (1983);
11. (b) R. D. Topson, Acc. Chem. Res. 16, 292 (1983).
12. W. Adcock and A. N. Abeywickrema, Tetrahedron Lett. 1809 (1979).
13. R. T. C. Brownlee and D. J. Craik, Tetrahedron Lett. 1681 (1980).
14. W. Adcock and A. N. Abeywickrema, J. Org. Chem. 47, 2945 (1982).
15. (a) W. Adcock, A. N. Abeywickrema and G. B. Kok, J. Org. Chem. 49, 1387 (1984);
16. (b) W. Adcock and V. S. Iyer, J. Org. Chem. 50, 1538 (1985);
17. (c) W. Adcock and G. B. Kok, J. Org. Chem. 52, 356 (1987);
18. (d) W. Adcock and V. S. Iyer, J. Org. Chem. 53, 5259 (1988);
19. (e) W. Adcock, A. R. Krstic, P. J. Duggan, V. J. Shiner, Jr, J. Coope and M. W. Ensinger, J. Am. Chem. Soc. 112, 3140 (1990);
20. (f) W. Adcock and N. A. Trout, J. Org. Chem. 56, 3229 (1991).
21. (a) R. Hoffmann, A. Imamura and W. J. Hehre, J. Am. Chem. Soc. 90, 1499 (1968);
22. (b) R. Hoffmann, Acc. Chem. Res. 4, 1 (1971);
23. (c) R. Gleiter, W.-D. Stohrer and R. Hoffmann, Helv. Chim. Acta 55, 893 (1972);
24. (d) B. Krijner, H. B. Beverloo, J. W. Verhoeven, C. A. Reiss, K. Goubitz and D. Heijdenrijk, J. Am. Chem Soc. 111, 4433 (1989) and references cited therein.
25. K. A. K. Ebraheem and G. A. Webb, Prog. Nucl. Magn. Reson. Spectrosc. 11, 149 (1977).
26. W. Adcock, G. Butt, G. B. Kok, S. Marriott and R. D. Topson, J. Org. Chem. 50, 2551 (1985).
27. W. Adcock, J. Cotton and N. A. Trout, J. Org. Chem. 59, 1867 (1994) and references cited therein.
28. M. J. S. Dewar and R. C. Dougherty, The PMO Theory of Organic Chemistry. Plenum Press, New York (1975).
29. N. D. Epiotis, W. R. Cherry, S. Shaik, R. L. Yates and F. Bernardi, Top. Curr. Chem. 70, 1 (1977).
30. See ref. 34 of ref. 9a.
31. A. J. Kirby, The Anomeric Effect and Related Stereoelectronic Effects at Oxygen. Springer, Berlin (1983).
32. See ref. 3 of ref. 9e.
33. W. Adcock and T. C. Khor, J. Am. Chem. Soc. 100, 7799 (1978).
34. W. Adcock and V. S. Iyer, Tetrahedron Lett. 25, 5209 (1984).
35. W. Adcock, N. J. Head, N. R. Lokan and N. A. Trout, J. Org. Chem. 62, 6177 (1997).
36. G. A. Olah, J. G. Shih, V. V. Krishnamurthy and B. P. Singh, J. Am. Chem. Soc. 106, 4492 (1984).
37. S. Srivastava, C. K. Cheung and W. le Noble, Magn. Reson. Chem. 23, 232 (1985).
38. D. Farcasiu, Synthesis 615 (1972).
39. E. J. Corey and M. Chaykovsky, J. Am. Chem. Soc. 87, 1353 (1965).
40. E. R. H. Jones, K. Bowden, I. M. Heilbron and B. C. L. Weedon, J. Chem. Soc. 39 (1946).
41. (a) O. H. Oldenziel and A. M. van Leusen, Tetrahedron Lett. 1357 (1973);
42. (b) O. H. Oldenziel, J. Wildemann and A. M. van Leusen, Org. Synth. 57, 8 (1977);
43. (c) O. H. Oldenziel, D. van Leusen and A. M. van Leusen, J. Org. Chem. 42, 3114 (1977).
44. B. E. Hoogenboom, O. H. Oldenziel and A. M. van Leusen, Org. Synth. 57, 102 (1977).
45. W. Adcock and C. I. Clark, J. Org. Chem. 58, 7341 (1993).
46. F. Campagna, A. Carrotti and G. Casini, Tetrahedron Lett. 1813 (1977).
47. A. S. Radhakrishna, C. G. Rao, R. R. Varma, B. B. Singh and S. P. Bhatnagar, Synthesis 538 (1983).
48. N. Kornblum and W. J. Jones, Org. Synth. 43, 87 (1963).
49. P. Golitz and A. Meijere, Angew. Chem., Int. Ed. Engl. 16, 854 (1977).
50. (a) W. Adam, J. Bialas and L. Hadjiarapoglou, Chem. Ber. 124, 2377 (1991);
51. (b) R. W. Murray, R. Jeyaraman and L. Mohan, Tetrahedron Lett. 27, 2335 (1986);
52. (c) R. W. Murray, S. N. Rajadhyaksha and L. Mohan, J. Org. Chem. 54, 5783 (1989).
53. D. H. R. Barton and G. Fontana, Tetrahedron 52, 11163 (1996) and references cited therein.