Conformation of chiral alkoxyallenes by proton NMR spectroscopy

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 1, 2000, Pages 61-67

  Lysek, Robert ^a   Krajewski, Piotr ^a   Urbańczyk Lipkowska, Zofia ^a   Furman, Bartlomiej ^a   Kaluza, Zbigniew ^a   Kozerski, Lech ^a   Chmielewski, Marek ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

CONFORMATIONS; GROUND STATE; MOLECULAR DYNAMICS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OLEFINS; REACTION KINETICS; SUBSTITUTION REACTIONS; X RAY ANALYSIS;

ALLENE; ALLENYL SUBSTITUTED FURANOSES; CHIRAL ALKOXYALLENES; MOLECULAR MECHANICS; X RAY STRUCTURE ANALYSIS;

AROMATIC COMPOUNDS;

EID: 0033993088     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (54)

1. R. Zimmer, Synthesis, 1993, 165.
2. H. F. Schuster and G. M. Copola, Allenes in Organic Synthesis, John Wiley & Sons, New York, 1984.
3. N. Miyaura, T. Yoshinari, M. Itoh and A. Suzuki, Tetrahedron Lett., 1980, 21, 537
4. D. Seyferth, C. M. Archer and J. C. Dewan, J. Organomet. Chem., 1986, 308, C5
5. D. Seyferth, L. L. Anderson and W. M. Davies, Organometallics, 1989, 8, 1371
6. S. Hormuth and H.-U. Reissig, Synlett, 1991, 179
7. P. Rochet, J.-M. Vatele and J. Goré, Synlett, 1993, 105
8. S. Hormuth and H.-U. Reissig, J. Org. Chem., 1994, 59, 67
9. M. A. Tius, Ch.-K. Kwok, X.-g. Gu and Ch. Zhao, Synth. Commun., 1994, 24, 871
10. V. J. Santora and H. W. Moore, J. Am. Chem. Soc., 1995, 117, 8486
11. N. A. Nedolya, L. Brandsma, W. P. Zinovieva and B. A. Trofimov, Zh. Org. Khim., 1997, 33, 91
12. N. A. Nedolya, L. Brandsma, O. A. Tarasova, H. D. Verkruijsse and B. A. Trofimov, Tetrahedron Lett., 1998, 39, 2409.
13. R. W. Hoffmann, J. Lanz, R. Metternich, G. Tarara and D. Hoppe, Angew. Chem., Int. Ed. Engl., 1987, 26, 1145
14. J.-F. Normant, J.-Ch. Quirion, A. Alexakis and Y. Masuda, Tetrahedron Lett., 1989, 30, 3955
15. J.-F. Normant, J.-Ch. Quirion, Y. Masuda and A. Alexakis, Tetrahedron Lett., 1990, 31, 2879
16. K. Koerber, J. Gore and J.-M. Vatele, Tetrahedron Lett., 1991, 32, 1187
17. T. N. Mitchell and U. Schneider, J. Organomet. Chem., 1991, 405, 195
18. I. Marek, A. Alexakis, P. Mangeney and J.-F. Normant, Bull. Soc. Chim. Fr., 1992, 129, 171
19. R. Grigg and J. M. Sansano, Tetrahedron, 1996, 52, 13441
20. C. Anies, J.-Y. Lallemand and A. Pancrazi, Tetrahedron Lett., 1996, 37, 5519
21. D. Hideura, H. Urabe and F. Sato, Chem. Commun., 1998, 271
22. Y. Yamamoto, Pure Appl. Chem., 1996, 68, 9.
23. D. L. Boger and A. M. Kasper, J. Am. Chem. Soc., 1989, 111, 1517
24. D. L. Boger and T. T. Curran, J. Org. Chem., 1990, 55, 5439
25. M. Conrads and J. Mattay, Chem. Ber., 1991, 124, 1425
26. R. Zimmer and H.-U. Reissig, Liebigs Ann. Chem., 1991, 553
27. T. Arnold, B. Orschel and H.-U. Reissig, Angew. Chem., Int. Ed. Engl., 1992, 31, 1033
28. G. Capozzi, R. W. Franck, M. Mattioli, S. Menichetti, C. Natavi and G. Valle, J. Org. Chem., 1995, 60, 6416
29. R. Zimmer, J. Angermann, U. Hain, F. Hiller and H.-U. Reissig, Synthesis, 1997, 1467.
30. J. J. Tufariello, 1.3-Dipolar Cycloaddition Chemistry, Ed. A. Padwa, John Wiley & Sons, New York, 1984, p. 83
31. A. Padwa, W. H. Bullock, D. N. Kline and J. Perumattam, J. Org. Chem., 1989, 54, 2862
32. M. Hojo, H. Aihara, H. Ito and A. Hosomi, Tetrahedron Lett., 1996, 37, 9241
33. M. Hojo, H. Aihara and A. Hosomi, J. Am. Chem. Soc., 1996, 118, 3533
34. M. Frederickson, Tetrahedron, 1997, 53, 403.
35. N. J. Koole, M. J. A. de Bie and P. E. Hansen, Org. Magn. Reson., 1984, 22, 146.
36. Z. Kałuza, B. Furman, M. Patel and M. Chmielewski, Tetrahedron: Asymmetry, 1994, 5, 2179
37. B. Furman, Z. Kałuza and M. Chmielewski, Tetrahedron, 1996, 52, 6019
38. R. Łysek, Z. Kałuza, B. Furman and M. Chmielewski, Tetrahedron, 1998, 54, 14065.
39. O. Neuß, B. Furman, Z. Kałuza and M. Chmielewski, Heterocycles, 1997, 45, 265
40. B. Furman, Z. Kałuza and M. Chmielewski, J. Org. Chem., 1997, 62, 3135.
41. B. Furman, P. Krajewski, Z. Kałuza, R. Thürmer, W. Voelter, L. Kozerski, M. P. Williamson and M. Chmielewski, J. Chem. Soc., Perkin Trans. 2, 1999, 217.
42. The table of final fractional atomic coordinates, the full list of bond lengths and angles and the list of thermal parameters have been deposited at the Cambridge Crystallographic Data Centre.§
43. D. Neuhaus and M. P. Williamson, The Nuclear Overhauser Effect in Structural and Conformational Analysis, VCH, New York, 1989.
44. L. Kozerski, R. Kawȩcki, P. Krajewski, P. Gluziñski, K. Pupek, P. E. Hansen and M. P. Williamson, J. Org. Chem., 1995, 60, 3533.
45. PCMODEL, Molecular modelling software, Serena Software, PO Box 3076, Bloomington, IN 47402-3076.
46. K. Stott, J. Keeler, Q. N. Van and A. J. Shaka, J. Magn. Reson., 1997, 125, 302.
47. W. Sowa, Can. J. Chem., 1968, 46, 1586.
48. M. Spescha, Helv. Chim. Acta, 1993, 76, 1832.
49. B. Hildebrandt, Y. Nakamura and S. Ogawa, Carbohydr. Res., 1991, 214, 87.
50. R. E. Ireland, S. Thaisrivongs, N. Vanier and C. S. Wilkox, J. Org. Chem., 1980, 45, 48.
51. M. Xie, D. A. Berges and M. J. Robins, J. Org. Chem., 1996, 61, 5178.
52. G. M. Sheldrick, SHELXS-86, Program for Crystal Structure Solution, University of Goettingen, Germany, 1986.
53. G. M. Sheldrick, SHELXL-97, Program for Crystal Structure Refinement, University of Goettingen, Germany, 1997.
54. L. Kozerski, R. Kawȩcki and P. E. Hansen, Magn. Reson. Chem., 1994, 32, 517.