Perturbations by phenyl on the 1,5-hydrogen shift in 1,3(Z)-pentadiene. Another chameleonic transition region?

Journal of the American Chemical Society

Volumn 126, Issue 43, 2004, Pages 14206-14216

  Doering, William Von E ^a   Keliher, Edmund J ^a   Zhao, Xin ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ENERGY; PERTURBATION TECHNIQUES;

CYCLIC SYSTEMS; HYDROGEN SHIFTS; RADICAL-STABILIZING; STABILIZING EFFECTS;

HYDROGEN;

1 PHENYL 5 (4 TOLYL) 1,3 PENTADIENE; ALKADIENE; HYDROGEN; UNCLASSIFIED DRUG;

ACCELERATION; ARTICLE; CONFORMATION; ENERGY; PRECURSOR; SUBSTITUTION REACTION;

EID: 7444221838     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja040106k     Document Type: Article

References (58)

1. 5 and in Dieter Hasselmann, Houben-Weyl, Methods of Organic Chemistry; Thieme: Stuttgart, 1995; Vol. E 21d, 4421-4430.
2. 5 and in Dieter Hasselmann, Houben-Weyl, Methods of Organic Chemistry; Thieme: Stuttgart, 1995; Vol. E 21d, 4421-4430.
3. Doering, W. v. E.; Wang, Y.-h. J. Am. Chem. Soc. 1999, 121, 10112-10118.
4. Hrovat, D. A.; Beno, B. R.; Lange, H.; Yoo, H.-y.; Houk, K. N.; Borden, W. T. J. Am. Chem. Soc. 1999, 121, 10529-10537.
5. -1.
6. Hess, B. A., Jr.; Baldwin, J. E. J. Org. Chem. 2002, 67, 6025-6033.
7. The parent model for the 1,5-hydrogen shift is the transfer of a hydrogen atom between methane and a methyl radical. A closer analogy would be the uninvestigated transfer from the methyl group of propene to an allyl radical.
8. (a) Ma, X.-I.; Schobert, H. H. Ind. Eng. Chem. Res. 2003, 42, 1151-1161.
9. (b) Camaioni, D. M.; Autrey, S. T.; Salinas, T. B.; Franz, J. A. J. Am. Chem. Soc. 1996, 118, 2013-2022.
10. Doering, W. v. E.; Birladeanu, L.; Sarma, K.; Teles, J. H.; Klärner, F.-G.; Gehrke, J.-S. J. Am. Chem. Soc. 1994, 116, 4289-4297.
11. Enklaar, C. J. Recl. Trav. Chim. Pays-Bas 1907, 26, 157-179.
12. Wolinsky, J.; Chollar, B.; Baird, M. D. J. Am. Chem. Soc. 1962, 84, 2775-2779.
13. Woodward, R. B.; Hoffmann, R. J. Am. Chem. Soc. 1965, 87, 2511-2513.
14. (a) Roth, W. R.; König, J. Liebigs Ann. Chem. 1966, 699, 24-32.
15. (b) Roth, W. R Chimia 1966, 20, 229-264.
16. (c) Roth, W. R.; König, J.; Stein, K. Chem. Ber. 1970, 103, 426-439.
17. D at the three temperatures given (°C), 195.1°, 5.22; 200.0°, 4.97; 205.3°, 5.11, to 25°C is not justifiable. This footnote may be of interest to the several theoretical chemists who have been stimulated by this apparently large deuterium isotope effect.
18. Rohse, N. Substituenteneffekte auf die 1,5-Pentadienylwasserstoff- verschiebung, PhD Dissertation, Abteilung für Chemie der Ruhr-Universität, Bochum, Germany (Roth, W. R, research sponsor), 1986.
19. Schlief, M. Substituenteneffekte auf die 1,5-Pentadienylwasserstoff- verschiebung in Cycloheptatriene, PhD Dissertation, Abteilung für Chemie der Ruhr-Universität, Bochum, Germany (Roth, W. R, research sponsor), 1990.
20. Dewar, J. M. S.; McDougherty, R. C. The PMO Theory of Organic Chemistry, Plenum Press: New York, 1975.
21. Saettel, N. J.; Wiest, O. J. Org. Chem. 2000, 65, 2331-2336.
22. Seetula, J. A.; Russell, J. J.; Gutman, D. J. Am. Chem. Soc. 1990, 112, 1347-1353.
23. Carpenter, J. E.; Sosa, C. P. THEOCHEM 1994, 311, 325-330.
24. CambridgeSoft Corporation, 100 CambridgePark Drive, Cambridge, MA 02140: ChemBats3D PRO, version 5.0.
25. Hayase, S.; Hrovat, D. A.; Borden, W. T. J. Am. Chem. Soc. 2004, 126, 10028-10034.
26. Doering, W. v. E.; Benkhoff, J.; Carleton, P. S.; Pagnotta, M. J. Am. Chem. Soc. 1997, 119, 10947-10955.
27. As a short-hand, idiosyncratic notation expressing the two positions between which substituents are distributed by the reversible 1,5-hydrogen shift; 5(1), for example, indicating reaction from the educt, 1(5) indicating the reverse reaction of the product.
28. Frey, H. M.; Pope, B. M. J. Chem. Soc. A 1966, 1701-1702.
29. O'Neal, H. E.; Frey, H. M.; Pope, B. M. Int. J. Chem. Kinet. 1970, 2, 343-347.
30. (a) Frey, H. M.; Ellis, R. J. J. Chem. Soc. A 1965, 4770-4773.
31. (b) Glass, D. S.; Boikess, R. S.; Winstein, S. Tetrahedron Lett. 1966, 999-1008.
32. Frey, H. M.; Solly, R. K. J. Chem. Soc. A 1969, 733-735.
33. Frey, H. M.; Lamont, A. M.; Walsh, R. J. Chem. Soc. A 1971, 2642-2646.
34. -1).
35. Bushby, R. J.; Farber, A. M. J. Chem. Soc., Perkin Trans. II 1976, 1695-1700.
36. -1 than our experimental value. It seems unlikely that the discrepancy can be attributed to the perturbation by p-methyl of one of the two phenyl groups.
37. Van-Catledge, F. A.; Boerth, D. W.; Kao, J. J. Org. Chem. 1982, 47, 4096-4106.
38. Kabalka, G. W.; Mohammadi, M.; Hylarides, M.; Finn, R. D. Org. Prep. Prod. Int. 1984, 16, 321-328.
39. The specific rate constant at 131.7°C is omitted from the calculation because its inclusion increases the standard error by more than a factor of 3.
40. (a) Riahi, A.; Thorey, C.; Hénin, F.; Muzart, J. Synth. Commun. 1998, 28, 4339-4344.
41. (b) Negishi, E.; Copéret, C.; Ma, S.; Mita, T.; Sugihara, T.; Tour, J. M. J. Am. Chem. Soc. 1996, 118, 5904-5918.
42. (c) Enders, D.; Zhu, J.; Kramps, L. Liebigs Ann/Recueil 1997, 1101-1113.
43. Petasis, N. A.; Bzowej, E. I. J. Am. Chem. Soc. 1990, 112, 6392-6394.
44. Kinder, F. R., Jr.; Chen. C.-P.; Bair, K. W. Synth. Commun. 1997, 27, 871-881.
45. (a) Doering, W. v. E.; Rosenthal, J. W. J. Am. Chem. Soc. 1967, 89, 4534.
46. (b) Grimme, W.; Pohl, V.; Wortmann, J.; Frowein, D. Liebigs Ann. 1996, 1905-1916.
47. (c) Corey, E. J.; Pasto, D. J.; Mock, W. L. J. Am. Chem. Soc. 1961, 83, 2957-2958.
48. (d) Houk, K. N.; Li, Y.; Evanseck, J. D. Angew. Chem., Int. Ed. Engl. 1992, 31, 682-708.
49. (e) Houk, K. N.; Li, Y.; McAllister, M. A.; O'Doherty, G.; Paquette, L. A.; Siebrand, W.; Smedarchina, Z. K. J. Am. Chem. Soc. 1994, 116, 10895-10914.
50. Pedley, J. B.; Naylor, R. D.; Kirby, S. P. Thermochemical Data of Organic Compounds, 2nd ed.; Chapman and Hall: London, 1986.
51. Doering, W. v. E.; Roth, W. R.; Bauer, F.; Breuckmann, R.; Ebbrecht, T.; Herbold, M.; Schmidt, R.; Lennartz, H.-W.; Lenoir, D.; Boese, R. Chem. Ber. 1989, 122, 1263-1275.
52. Korth, H. G.; Trill, R.; Sustmann, R. J. Am. Chem. Soc. 1981, 103, 4483-4489.
53. -1; Roth, W. R Tetrahedron Lett. 1964, 1009) reported by Baldwin and Reddy for the 1,7-hydrogen shift in hepta-1,(Z)3(Z)5-triene. Although the comparison of the antarafacial, helical eight-membered transition region with the suprafacial, planar six-membered 1,5-hydrogen shift is problematic in several ways, the crucial, core element has essentially become linear.
54. Baldwin, J. E.; Reddy, V. P. J. Am. Chem. Soc. 1988, 110, 8223-8228.
55. 7a we are not engaging in assessment of the accuracy of these values.
56. Doering, W. v. E.; Benkhoff, J.; Shao, L.-m. J. Am. Chem. Soc. 1999, 121, 962-968.
57. Hayase, S.; Hrovat, D. A.; Borden, W. T. Unpublished results (with permission to quote).
58. Donahue, M.; Staples, R. J. X-ray Crystallographic Laboratory, Harvard University, unpublished.