Hyperconjugation involving strained carbon-carbon bonds. Structural analysis of ester and ether derivatives and one-bond 13C- 13C coupling constants of α- And β-nopinol

Journal of Organic Chemistry

Volumn 78, Issue 2, 2013, Pages 311-319

  Yeoh, Shinn Dee ^a   Skene, Colin E ^a   White, Jonathan M ^a  

^a UNIVERSITY OF MELBOURNE   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

BOND DISTANCE; BOND STRENGTHENING; C-C BONDS; CARBON-CARBON BOND; COUPLING CONSTANTS; ETHER DERIVATIVES; HYPERCONJUGATION; HYPERCONJUGATIVE INTERACTIONS; OXYGEN PROBES;

ESTERIFICATION; ESTERS; ETHERS; X RAY CRYSTALLOGRAPHY;

COVALENT BONDS;

ALPHA NOPINOL; BEAT NOPINOL; CARBON 13; ESTER DERIVATIVE; ETHER DERIVATIVE; TERPENE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; CONJUGATION; X RAY CRYSTALLOGRAPHY;

BRIDGED COMPOUNDS; CARBON; CARBON ISOTOPES; CRYSTALLOGRAPHY, X-RAY; ESTERS; ETHERS; MODELS, MOLECULAR; QUANTUM THEORY;

EID: 84872555467     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo3020243     Document Type: Article

References (48)

1. White, J. M., Clark, C. I. Topics in Stereochemistry; Denmark, S. E., Ed.; John Wiley and Sons: New York, 1999; Vol. 22, Chapter 3.
2. Murakami, M. Angew. Chem., Int. Ed. 2001, 189
3. Johnson, C. D. Acc. Chem. Res. 1993, 26, 476
4. Kirby, A. J. The Anomeric Effect and Related Stereoelctronic Effects at Oxygen; Springer Verlag: Berlin, 1983.
5. Jensen, H. H. Acc. Chem. Res. 2006, 39, 259
6. Thatcher, G. R. J. The Anomeric Effect and Associated Stereoelectronic Effects: Developed from a Symposium Sponsored by the Division of Carbohydrate Chemistry at the 204th National Meeting of the American Chemical Society, Washington, DC, Aug 23-28, 1992.
7. Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Baldwin, J. E., Ed.; Pergamon Press: New York, 1983; Organic Chemistry Series Vol. 1.
8. Mulliken, R. S. J. Chem. Phys. 1939, 7, 339
9. Egorochkin, A. N. Russ. Chem. Rev. 1984, 53, 445
10. Gleiter, R. Pure Appl. Chem. 1987, 59, 1585
11. Muller, N.; Mulliken, R. S. J. Am. Chem. Soc. 1958, 80, 3489
12. Davis, D. D. J. Organomet. Chem. 1981, 206, 21
13. Cook, M. A.; Eaborn, C.; Walton, D. R. M. J. Organomet. Chem. 1970, 24, 293
14. Hanstein, W.; Berwin, H. J.; Traylor, T. G. J. Am. Chem. Soc. 1970, 92, 829
15. Adcock, W.; Cox, D. P.; Kitching, W. J. Organomet. Chem. 1977, 133, 393
16. Alabugin, I. V. J. Org. Chem. 2000, 65, 3910
17. Pophristic, V.; Goodman, L. Nature 2001, 411, 565
18. Alabugin, I. V. J. Am. Chem. Soc. 2002, 124, 3175
19. Briggs, A. J.; Glenn, R.; Jones, P. G.; Kirby, A. J.; Ramaswamy, P. J. Am. Chem. Soc. 1984, 106, 6200
20. Amos, R. D.; Handy, N. C.; Jones, P. G.; Kirby, A. J.; Parker, J. K.; Percy, J. M.; Su, M. D. J. Chem. Soc., Perkin Trans. 2 1992, 4, 549
21. Green, A. J.; Giordano, J.; White, J. M. Aust. J. Chem. 2000, 53, 285
22. Spiniello, M.; White, J. M. Org. Biomol. Chem. 2003, 1, 3094
23. Kirby, A. J. The Anomeric Effect and Related Stereoelectronic Effects at Oxygen; Springer-Verlag: Berlin, 1983.
24. The Anomeric Effect and Associated Stereoelectronic Effects; Thatcher, G. R. W., Ed; ACS Symposium Series 539; American Chemical Society: Washington, DC, 1993.
25. Lambert, J. B. Tetrahedron 1990, 46, 2677
26. White, J. M.; Spiniello, M.; Jones, S.; Gable, R.; Lambert, J. B. Chem.-Eur. J. 2002, 8, 2799
27. Pool, B. R.; White, J. M.; Wolynec, P. J. Org. Chem. 2000, 65, 7505
28. Jackson, W.; White, J. M. Aust. J. Chem. 2008, 61, 956
29. King, J. F.; Mayo, P. Terpenoid Rearrangements. In Molecular Rearrangements; Mayo, P., Ed.; John Wiley and Sons: New York, 1968; pp 771-840.
30. Hanson, J. R. Wagner-Meerwein Rearrangements. In Comprehensive Organic Synthesis; Pergamon Press: Oxford, 1991; pp 705-719.
31. Wagner, G. J. Russ. Phys. Chem. 1899, 31, 680
32. Schleyer, P. v. R.; Watts, W. E.; Cupas, C. J. Am. Chem. Soc. 1964, 86, 2722
33. Winstein, S.; Holness, N. J. J. Am. Chem. Soc. 1955, 77, 3054
34. Uggerud, E.; Arad, D.; Apeloig, Y.; Swartz, H. J. Chem. Soc., Chem. Commun. 1989, 1015
35. Clinton, N. A.; Brown, R. S.; Traylor, T. G. J. Am. Chem. Soc. 1970, 92, 5228
36. Streitwieser, A., Jr.; Alexandratos, S. J. Am. Chem. Soc. 1978, 100, 1979
37. Stirling, A. J. M. Tetrahedron 1985, 1613
38. Rauk, A. Orbital Interaction Theory of Organic Chemistry, 2 nd ed.; John Wiley & Sons: New York, 2000.
39. Lide, D. R. CRC Handbook of Chemistry and Physics, 79 th ed.; CRC Press LLC: Boca Raton, FL, 1998.
40. Dean, J. A. Lange's Handbook of Chemistry, 14 th ed.; McGraw-Hill: New York, 1992.
41. Bucourt, R. Top. Stereochem. 1974, 8, 159
42. White, J. M.; Fifer, N. Org. Biomol. Chem. 2005, 3, 1776
43. Unkefer, C. J.; London, R. E.; Whaley, T. W.; Daub, G. H. J. Am. Chem. Soc. 1983, 105, 733
44. Vogel, P. Helv. Chim. Acta 1997, 80, 59
45. Hansen, P. E. Annu. Rep. NMR Spectrosc. 1981, 11A, 65-98
46. Duddeck, H.; Hollowood, F.; Karim, A.; McKervey, M. A. J. Chem. Soc., Perkin Trans. 2 1979, 360
47. Goh, Y. W.; Danczak, S. M.; Lim, T. K.; White, J. M. J. Org. Chem. 2007, 72, 2929
48. Baretta, A.; Jefford, C. W.; Waegell, B. Bull. Soc. Chim. Fr. 1970, 11, 3985-93