Conformational studies by dynamic NMR. 70. Stereomutations of homochiral dicarvone in solution and in the solid state

Journal of Organic Chemistry

Volumn 65, Issue 3, 2000, Pages 883-888

  Lunazzi, Lodovico ^a   Mazzanti, Andrea ^a   Casarini, Daniele ^b   De Lucchi, Ottorino ^c   Fabris, Fabrizio ^c  

^a UNIVERSITY OF BOLOGNA   (Italy)

^b UNIVERSITY OF BASILICATA   (Italy)

^c CA' FOSCARI UNIVERSITY OF VENICE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CARVONE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CHIRALITY; CONFORMATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS; X RAY DIFFRACTION;

EID: 0033953748     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9913964     Document Type: Article

References (36)

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16. 3OD at the same temperature.
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20. The proportions were found to be 8% at -99°C and 9.5% at -88°C.
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25. 3
26. The shift deviations are due not only to the different temperatures and phases, but also to the different methods employed to determine the shifts in solution and in the solid state (for the latter see the Experimental Section).
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28. Miller, R. D.; Yannoni, C. S. J. Am. Chem. Soc. 1980, 102, 7396. Elguero, J.; Fruchier, A.; Pellegrin, V. J. Chem. Soc., Chem. Commun. 1981, 1207. Riddell, F. G.; Arumagam, S.; Anderson, J. E. J. Chem. Soc., Chem. Commun. 1991, 1525. Lambert, J. B.; Xue, L.; Howton, S. C. J. Am. Chem. Soc. 1991, 113, 8958. Barrie, P. J.; Anderson, J. E. J. Chem. Soc., Perkin Trans. 2 1992, 2031. Riddell, F. G.; Arumagam, S.; Harris, K. D. M.; Rogerson, M.; Strange, J. H. J. Am. Chem. Soc. 1993, 115, 1881. Riddell, F. G.; Cameron, K. S.; Holmes, S. A.; Strange, J. H. J. Am. Chem. Soc. 1997, 119, 7555. Casarini, D.; Lunazzi, L.; Mazzanti, A. J. Org. Chem. 1998, 63, 9125.
29. Miller, R. D.; Yannoni, C. S. J. Am. Chem. Soc. 1980, 102, 7396. Elguero, J.; Fruchier, A.; Pellegrin, V. J. Chem. Soc., Chem. Commun. 1981, 1207. Riddell, F. G.; Arumagam, S.; Anderson, J. E. J. Chem. Soc., Chem. Commun. 1991, 1525. Lambert, J. B.; Xue, L.; Howton, S. C. J. Am. Chem. Soc. 1991, 113, 8958. Barrie, P. J.; Anderson, J. E. J. Chem. Soc., Perkin Trans. 2 1992, 2031. Riddell, F. G.; Arumagam, S.; Harris, K. D. M.; Rogerson, M.; Strange, J. H. J. Am. Chem. Soc. 1993, 115, 1881. Riddell, F. G.; Cameron, K. S.; Holmes, S. A.; Strange, J. H. J. Am. Chem. Soc. 1997, 119, 7555. Casarini, D.; Lunazzi, L.; Mazzanti, A. J. Org. Chem. 1998, 63, 9125.
30. Miller, R. D.; Yannoni, C. S. J. Am. Chem. Soc. 1980, 102, 7396. Elguero, J.; Fruchier, A.; Pellegrin, V. J. Chem. Soc., Chem. Commun. 1981, 1207. Riddell, F. G.; Arumagam, S.; Anderson, J. E. J. Chem. Soc., Chem. Commun. 1991, 1525. Lambert, J. B.; Xue, L.; Howton, S. C. J. Am. Chem. Soc. 1991, 113, 8958. Barrie, P. J.; Anderson, J. E. J. Chem. Soc., Perkin Trans. 2 1992, 2031. Riddell, F. G.; Arumagam, S.; Harris, K. D. M.; Rogerson, M.; Strange, J. H. J. Am. Chem. Soc. 1993, 115, 1881. Riddell, F. G.; Cameron, K. S.; Holmes, S. A.; Strange, J. H. J. Am. Chem. Soc. 1997, 119, 7555. Casarini, D.; Lunazzi, L.; Mazzanti, A. J. Org. Chem. 1998, 63, 9125.
31. Miller, R. D.; Yannoni, C. S. J. Am. Chem. Soc. 1980, 102, 7396. Elguero, J.; Fruchier, A.; Pellegrin, V. J. Chem. Soc., Chem. Commun. 1981, 1207. Riddell, F. G.; Arumagam, S.; Anderson, J. E. J. Chem. Soc., Chem. Commun. 1991, 1525. Lambert, J. B.; Xue, L.; Howton, S. C. J. Am. Chem. Soc. 1991, 113, 8958. Barrie, P. J.; Anderson, J. E. J. Chem. Soc., Perkin Trans. 2 1992, 2031. Riddell, F. G.; Arumagam, S.; Harris, K. D. M.; Rogerson, M.; Strange, J. H. J. Am. Chem. Soc. 1993, 115, 1881. Riddell, F. G.; Cameron, K. S.; Holmes, S. A.; Strange, J. H. J. Am. Chem. Soc. 1997, 119, 7555. Casarini, D.; Lunazzi, L.; Mazzanti, A. J. Org. Chem. 1998, 63, 9125.
32. Miller, R. D.; Yannoni, C. S. J. Am. Chem. Soc. 1980, 102, 7396. Elguero, J.; Fruchier, A.; Pellegrin, V. J. Chem. Soc., Chem. Commun. 1981, 1207. Riddell, F. G.; Arumagam, S.; Anderson, J. E. J. Chem. Soc., Chem. Commun. 1991, 1525. Lambert, J. B.; Xue, L.; Howton, S. C. J. Am. Chem. Soc. 1991, 113, 8958. Barrie, P. J.; Anderson, J. E. J. Chem. Soc., Perkin Trans. 2 1992, 2031. Riddell, F. G.; Arumagam, S.; Harris, K. D. M.; Rogerson, M.; Strange, J. H. J. Am. Chem. Soc. 1993, 115, 1881. Riddell, F. G.; Cameron, K. S.; Holmes, S. A.; Strange, J. H. J. Am. Chem. Soc. 1997, 119, 7555. Casarini, D.; Lunazzi, L.; Mazzanti, A. J. Org. Chem. 1998, 63, 9125.
33. Miller, R. D.; Yannoni, C. S. J. Am. Chem. Soc. 1980, 102, 7396. Elguero, J.; Fruchier, A.; Pellegrin, V. J. Chem. Soc., Chem. Commun. 1981, 1207. Riddell, F. G.; Arumagam, S.; Anderson, J. E. J. Chem. Soc., Chem. Commun. 1991, 1525. Lambert, J. B.; Xue, L.; Howton, S. C. J. Am. Chem. Soc. 1991, 113, 8958. Barrie, P. J.; Anderson, J. E. J. Chem. Soc., Perkin Trans. 2 1992, 2031. Riddell, F. G.; Arumagam, S.; Harris, K. D. M.; Rogerson, M.; Strange, J. H. J. Am. Chem. Soc. 1993, 115, 1881. Riddell, F. G.; Cameron, K. S.; Holmes, S. A.; Strange, J. H. J. Am. Chem. Soc. 1997, 119, 7555. Casarini, D.; Lunazzi, L.; Mazzanti, A. J. Org. Chem. 1998, 63, 9125.
34. Miller, R. D.; Yannoni, C. S. J. Am. Chem. Soc. 1980, 102, 7396. Elguero, J.; Fruchier, A.; Pellegrin, V. J. Chem. Soc., Chem. Commun. 1981, 1207. Riddell, F. G.; Arumagam, S.; Anderson, J. E. J. Chem. Soc., Chem. Commun. 1991, 1525. Lambert, J. B.; Xue, L.; Howton, S. C. J. Am. Chem. Soc. 1991, 113, 8958. Barrie, P. J.; Anderson, J. E. J. Chem. Soc., Perkin Trans. 2 1992, 2031. Riddell, F. G.; Arumagam, S.; Harris, K. D. M.; Rogerson, M.; Strange, J. H. J. Am. Chem. Soc. 1993, 115, 1881. Riddell, F. G.; Cameron, K. S.; Holmes, S. A.; Strange, J. H. J. Am. Chem. Soc. 1997, 119, 7555. Casarini, D.; Lunazzi, L.; Mazzanti, A. J. Org. Chem. 1998, 63, 9125.
35. 3) of the very same crystals examined in the CP-MAS experiment showed that the impurities do not exceed 1.5%, an amount definitely too small to be detectable with the signal-to-noise ratio of the -40°C spectrum of Figure 4.
36. Private communication of Dr. G. Valle, CNR, Padua.