Regioselective synthesis and Diels-Alder reaction of 3,4-dimethylpenta- 1,3-diene. Conformational study of bicyclic adducts structures by 1H NMR (NOESY, ASIs) and molecular modeling (MM2, AM1, RHF, and DFT)

Journal of Organic Chemistry

Volumn 64, Issue 26, 1999, Pages 9557-9565

  Gosselin, Pascal ^a   Bourdy, Christophe ^a   Mille, Stéphane ^a   Perrotin, Angélique ^a  

^a UNIVERSITÉ DU MAINE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

3,4 DIMETHYLPENTA 1,3 DIENE; ALKADIENE; BICYCLO COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION KINETICS; CONFORMATION; HYDROLYSIS; MOLECULAR MODEL; ORGANIC CHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033601244     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991173d     Document Type: Article

References (58)

1. Chapuis, Ch. Tetrahedron Lett. 1991, 32, 355.
2. Ohloff, G. Scent and Fragrances; Springer-Verlag: Berlin, Heidelberg, 1994; pp 164-166.
3. Nazarov, I. N.; Mavrov, M. V. Doklady Akad. Nauk S.S.S.R. 1958, 120, 86 (Chem. Abstr. 1958, 52, 20021e).
4. Nazarov, I. N.; Mavrov, M. V. Doklady Akad. Nauk S.S.S.R. 1958, 120, 86 (Chem. Abstr. 1958, 52, 20021e).
5. Nazarov, I. N.; Mavrov, M. V. Zh. Obshchei Khim. 1959, 29, 1158 (Chem. Abstr. 1960, 54, 4353i).
6. Nazarov, I. N.; Mavrov, M. V. Zh. Obshchei Khim. 1959, 29, 1158 (Chem. Abstr. 1960, 54, 4353i).
7. Nishida, T.; Arai, A.; Ichikizaki, I. Bull. Chem. Soc. Jpn. 1962, 35, 572.
8. Goldman, N. L. Chem. Ind. (London) 1963, 25, 1036.
9. Ichikizaki, I.; Arai, A. Kobayashi Rigaku Ken Kyusho Hokoku 1963, 13 (3), 117 (Chem. Abstr. 1964, 67, 13206g).
10. Ichikizaki, I.; Arai, A. Kobayashi Rigaku Ken Kyusho Hokoku 1963, 13 (3), 117 (Chem. Abstr. 1964, 67, 13206g).
11. Ichikizaki, I.; Arai, A. Bull. Chem. Soc. Jpn. 1964, 37 (3), 432.
12. Arai, A.; Ichikizaki, I. Bull. Chem. Soc. Jpn. 1962, 35, 45.
13. Naves, Y. R.; Ardizio, P. Helv. Chim. Acta 1948, 31, 2252.
14. McIntosh, J. M.; Goodbrand, H. B.; Masse, G. M. J. Org. Chem. 1974, 39, 202.
15. Oppolzer, W.; Wylie, R. D. Helv. Chim. Acta 1980, 63, 1198 and references cited.
16. Vedejs, E.; Meier, G. P.; Snoble, K. A. J. J. Am. Chem. Soc. 1981, 103, 2823 and references cited.
17. Adlercreutz, P.; Magnusson, G. Acta Chem. Scand. 1980, B34, 647.
18. Julian, P. L.; Meyer, E. W.; Printy, H. C. J. Am. Chem. Soc. 1948, 70, 887.
19. Jacobi, P. A.; Brielmann, H. L.; Cann, R. O. J. Org. Chem. 1994, 59, 5305 and references cited.
20. Golding, B. T.; Pombo-Villar, E.; Samuel, C. J. J. Chem. Soc., Chem. Commun. 1985, 1444.
21. Ono, N.; Miyaka, H.; Tanikaga, R.; Kaji, A. J. Org. Chem. 1982, 47, 5017.
22. Blanco, L.; Amice, P.; Conia, J. M. Synthesis 1981, 4, 291.
23. Mueller-Cunradi, M.; Pieroh, K. U.S. Patent 2165962, 1939; Chem. Abstr. 1939, 33, 8210.
24. Mueller-Cunradi, M.; Pieroh, K. U.S. Patent 2165962, 1939; Chem. Abstr. 1939, 33, 8210.
25. Hoaglin, R. I.; Hirsh, D. H. J. Am. Chem. Soc. 1949, 71, 3468.
26. Fishman, D.; Klug, J. T.; Shani, A. Synthesis 1981, 2, 137 and references cited.
27. When the cheaper 2,2-dimethoxypropane was used instead of 8, a mixture of trialkoxybutanes was obtained which was hydrolyzed directly into aldehyde 7. In this way, overall yield of aldehyde 7 was slightly lower (44% in lieu of 48%).
28. Fitjer, L.; Quabeck, U. Synth. Commun. 1985, 15, 855.
29. Brion, F. Tetrahedron Lett. 1982, 23, 5299.
30. 10 P = 0.05223α/T + b where P is the pressure in mm of mercury of the saturated vapor at the absolute temperature T. For benzene: α = 32295, b = 7.6546 gives P ≅ 2.35 atms.
31. CRC Handbook of Chemistry and Physics, 64th ed.; Weast, R. C., Ed.; CRC Press: Boca Raton, FL, 1983-1984; p D-215.
32. (a) Frey, H. M.; Lamont, A. M.; Walsh, R. J. Chem. Soc. (A) 1971, 2642.
33. (b) One Reviewer drew our attention to a related thermal Z:E isomerization of a 2-cobalt-substituted-1,3-diene: Wright, M. W.; Welker, M. E. J. Org. Chem, 1996, 61, 133.
34. Wollweber, H. Houben-Weil, Methoden der Organischen Chemie, 4th ed.; Müller, E., Ed.; Georg Thieme Verlag: Stuttgart, 1970; Vol. V/1c, pp 1067-1068.
35. See, for instances: (a) Kozmin, S. A.; Janey, J. M.; Rawal, V. H. J. Org. Chem. 1999, 64, 3039. (b) Arce, E.; Carrenõ, M. C.; Cid, M. B.; García Ruano, J. L. J. Org. Chem. 1994, 59, 3421. Boehler, M. A.; Konopelski, J. P. Tetrahedron 1991, 47, 4519. Fisher, M. J.; Overman, L. E. J. Org. Chem. 1988, 53, 2630. (e) Overman, L. E.; Freerks, R. L.; Petty, C. B.; Clizbe, L. A.; One, R. K.; Taylor, G. F.; Jessup, P. J. J. Am. Chem. Soc. 1981, 103, 2816. (f) Danishefsky, S.; Kirahara, T. J. Am. Chem. soc. 1974, 96, 7807.
36. See, for instances: (a) Kozmin, S. A.; Janey, J. M.; Rawal, V. H. J. Org. Chem. 1999, 64, 3039. (b) Arce, E.; Carrenõ, M. C.; Cid, M. B.; García Ruano, J. L. J. Org. Chem. 1994, 59, 3421. Boehler, M. A.; Konopelski, J. P. Tetrahedron 1991, 47, 4519. Fisher, M. J.; Overman, L. E. J. Org. Chem. 1988, 53, 2630. (e) Overman, L. E.; Freerks, R. L.; Petty, C. B.; Clizbe, L. A.; One, R. K.; Taylor, G. F.; Jessup, P. J. J. Am. Chem. Soc. 1981, 103, 2816. (f) Danishefsky, S.; Kirahara, T. J. Am. Chem. soc. 1974, 96, 7807.
37. See, for instances: (a) Kozmin, S. A.; Janey, J. M.; Rawal, V. H. J. Org. Chem. 1999, 64, 3039. (b) Arce, E.; Carrenõ, M. C.; Cid, M. B.; García Ruano, J. L. J. Org. Chem. 1994, 59, 3421. Boehler, M. A.; Konopelski, J. P. Tetrahedron 1991, 47, 4519. Fisher, M. J.; Overman, L. E. J. Org. Chem. 1988, 53, 2630. (e) Overman, L. E.; Freerks, R. L.; Petty, C. B.; Clizbe, L. A.; One, R. K.; Taylor, G. F.; Jessup, P. J. J. Am. Chem. Soc. 1981, 103, 2816. (f) Danishefsky, S.; Kirahara, T. J. Am. Chem. soc. 1974, 96, 7807.
38. See, for instances: (a) Kozmin, S. A.; Janey, J. M.; Rawal, V. H. J. Org. Chem. 1999, 64, 3039. (b) Arce, E.; Carrenõ, M. C.; Cid, M. B.; García Ruano, J. L. J. Org. Chem. 1994, 59, 3421. Boehler, M. A.; Konopelski, J. P. Tetrahedron 1991, 47, 4519. Fisher, M. J.; Overman, L. E. J. Org. Chem. 1988, 53, 2630. (e) Overman, L. E.; Freerks, R. L.; Petty, C. B.; Clizbe, L. A.; One, R. K.; Taylor, G. F.; Jessup, P. J. J. Am. Chem. Soc. 1981, 103, 2816. (f) Danishefsky, S.; Kirahara, T. J. Am. Chem. soc. 1974, 96, 7807.
39. See, for instances: (a) Kozmin, S. A.; Janey, J. M.; Rawal, V. H. J. Org. Chem. 1999, 64, 3039. (b) Arce, E.; Carrenõ, M. C.; Cid, M. B.; García Ruano, J. L. J. Org. Chem. 1994, 59, 3421. Boehler, M. A.; Konopelski, J. P. Tetrahedron 1991, 47, 4519. Fisher, M. J.; Overman, L. E. J. Org. Chem. 1988, 53, 2630. (e) Overman, L. E.; Freerks, R. L.; Petty, C. B.; Clizbe, L. A.; One, R. K.; Taylor, G. F.; Jessup, P. J. J. Am. Chem. Soc. 1981, 103, 2816. (f) Danishefsky, S.; Kirahara, T. J. Am. Chem. soc. 1974, 96, 7807.
40. See, for instances: (a) Kozmin, S. A.; Janey, J. M.; Rawal, V. H. J. Org. Chem. 1999, 64, 3039. (b) Arce, E.; Carrenõ, M. C.; Cid, M. B.; García Ruano, J. L. J. Org. Chem. 1994, 59, 3421. Boehler, M. A.; Konopelski, J. P. Tetrahedron 1991, 47, 4519. Fisher, M. J.; Overman, L. E. J. Org. Chem. 1988, 53, 2630. (e) Overman, L. E.; Freerks, R. L.; Petty, C. B.; Clizbe, L. A.; One, R. K.; Taylor, G. F.; Jessup, P. J. J. Am. Chem. Soc. 1981, 103, 2816. (f) Danishefsky, S.; Kirahara, T. J. Am. Chem. soc. 1974, 96, 7807.
41. (a) Kemp, M. I.; Whitby, R. J.; Coote, S. J. Synthesis 1998, 4 Special Issue, 557.
42. (b) Maddaluno, J.; Gaonac'h, O.; Marcual, A.; Toupet, L.; Giessner-Prettre, C. J. Org. chem. 1996, 61, 5290.
43. (c) Danishefsky, S.; Yan, C. F.; Singh, R. K.; Gammill, R. B.; McCurry, P. M.; Fritsch, N.; Clardy, J. J. Am. Chem. Soc. 1979, 101, 7001.
44. 3. This proved the solvent-independent conformational stability of adducts 2 and 3.
45. Gaudemer, A. Stereochemistry, Fundamentals and Methods; Kagan, H. B., Ed.; Georg Thieme Publish.: Stuttgart, 1977; Vol. 1, p 102.
46. CAChe program (V. 3.9 for Powermacintosh): Oxford Molecular, Medawar Center, Oxford Science Park, Oxford, OX4 4GA, England.
47. MacSpartan Plus (V 1.2 for Powermacintosh): Wavefunction, Inc., 18401 Von Karman Ave., Ste. 370, Irvine, CA 92612.
48. Gaussian 94, Rev. E2: Gaussian, Inc.. Carnegie Office Park, Bldg. 6, Pittsburgh, PA 15106.
49. Bothner-By, A. A. Adv. Magn. Reson. 1965, 1, 195.
50. Balacco, G. J. Chem. Inf. Comput. Sci. 1996, 36, 885 and references therein.
51. Moreover, one of us (P. G.) already described it's successful application to a similar case: Gosselin, P.; Bonfand, E.; Hayes, P.; Retoux, R.; Maignan, C. Tetrahedron: Asymmetry 1994, 5, 781.
52. Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; John Wiley & Sons: New York, 1994; p 738.
53. Larter, R. M.; Craig, R. E. R.; Craig, A. C.; Mundy, B. P. J. Org. Chem. 1977, 42, 1259.
54. Stephenson, L. M.; Smith, D. E.; Current, S. P. J. Org. Chem. 1982, 47, 4170 and references therein.
55. gNMR (V. 3.6 for Powermacintosh): Cherwell Scientific Publishing Ltd, Magdalen Center, Oxford Science Park, Oxford, OX4 4GA, England.
56. Garbish, E. W. J. Am. Chem. Soc. 1964, 86, 5561.
57. Wittig, G.; Wittenberg, D. Justus Liebig Ann. Chem. 1957, 606, 18.
58. Flash chromatography should be avoided because it induced the opening of most of 2 into the corresponding diacid.