Quantification of nonstatistical dynamics in an intramolecular Diels-Alder cyclization without trajectory computation

Journal of Organic Chemistry

Volumn 79, Issue 6, 2014, Pages 2368-2376

  Samanta, Debabrata ^a   Rana, Anup ^a   Schmittel, Michael ^a  

^a UNIVERSITY OF SIEGEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROCARBONS; MOLECULES; REACTION INTERMEDIATES;

DFT COMPUTATIONS; DIELS-ALDER CYCLIZATION; DIRADICAL INTERMEDIATES; NONSTATISTICAL DYNAMICS; PRODUCT FORMATION; REACTION PATHS; SIMPLE PROTOCOL; TRANSITION STATE;

CYCLIZATION;

ALLENE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CYCLIZATION; DENSITY FUNCTIONAL THEORY; DIELS ALDER REACTION; MOLECULAR DYNAMICS; QUANTITATIVE ANALYSIS; SUBSTITUTION REACTION;

EID: 84896985432     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo500035b     Document Type: Article

References (58)

1. Eyring, H. J. Chem. Phys. 1935, 3, 107
2. Wigner, E. Trans. Faraday Soc. 1938, 34, 29
3. Kassel, L. S. Chem. Rev. 1932, 10, 11
4. Rice, O. K.; Ramsperger, H. C. J. Am. Chem. Soc. 1927, 49, 1617
5. Marcus, R. A. J. Chem. Phys. 1952, 20, 352
6. Marcus, R. A. J. Chem. Phys. 1952, 20, 355
7. Doubleday, C.; Li, G.; Hase, W. L. Phys. Chem. Chem. Phys. 2002, 4, 304
8. Thomas, J. B.; Waas, J. R.; Harmata, M.; Singleton, D. A. J. Am. Chem. Soc. 2008, 130, 14544
9. Rehbein, J.; Carpenter, B. K. Phys. Chem. Chem. Phys. 2011, 13, 20906
10. Carpenter, B. K. Chem. Rev. 2013, 113, 7265
11. Sun, L.; Song, K.; Hase, W. L. Science 2002, 296, 875
12. Bogle, X. S.; Singleton, D. A. Org. Lett. 2012, 14, 2528
13. Schmittel, M.; Vavilala, C.; Jaquet, R. Angew. Chem., Int. Ed. 2007, 46, 6911
14. Lan, Y.; Danheiser, R. L.; Houk, K. N. J. Org. Chem. 2012, 77, 1533
15. Nummela, J. A.; Carpenter, B. K. J. Am. Chem. Soc. 2002, 124, 8512
16. Zhou, J.; Schlegel, H. B. Theor. Chem. Acc. 2012, 131, 1126
17. Bach, A.; Hostettler, J. M.; Chen, P. J. Chem. Phys. 2006, 125, 024304
18. Broyles, D. A.; Carpenter, B. K. Org. Biomol. Chem. 2005, 3, 1757
19. Gasser, M.; Bach, A.; Chen, P. Phys. Chem. Chem. Phys. 2008, 10, 1133
20. Gasser, M.; Frey, J. A.; Hostettler, J. M.; Bach, A. Chem. Commun. 2011, 47, 301
21. Matute, R. A.; Houk, K. N. Angew. Chem., Int. Ed. 2012, 51, 13097
22. Katori, T.; Itoh, S.; Sato, M.; Yamataka, H. J. Am. Chem. Soc. 2010, 132, 3413
23. Itoh, S.; Yamataka, H. Chem.-Eur. J. 2011, 17, 1230
24. Itoh, S.; Yoshimura, N.; Sato, M.; Yamataka, H. J. Org. Chem. 2011, 76, 8294
25. Goldman, L. M.; Glowacki, D. R.; Carpenter, B. K. J. Am. Chem. Soc. 2011, 133, 5312
26. Akimoto, R.; Tokugawa, T.; Yamamoto, Y.; Yamataka, H. J. Org. Chem. 2012, 77, 4073
27. Schmittel, M.; Strittmatter, M.; Kiau, S. Tetrahedron Lett. 1995, 36, 4975
28. Schmittel, M.; Steffen, J.-P.; Rodríguez, D.; Engelen, B.; Neumann, E.; Cinar, M. E. J. Org. Chem. 2008, 73, 3005
29. Schmittel, M.; Vavilala, C.; Cinar, M. E. J. Phys. Org. Chem. 2012, 25, 182
30. Schmittel, M.; Kiau, S.; Siebert, T.; Strittmatter, M. Tetrahedron Lett. 1996, 37, 7691
31. Schmittel, M.; Maywald, M.; Strittmatter, M. Synlett 1997, 165
32. Zhang, H. -R.; Wang, K. K. J. Org. Chem. 1999, 64, 7996
33. Wang, K. K.; Zhang, H.-R.; Petersen, J. L. J. Org. Chem. 1999, 64, 1650
34. Dai, W.; Petersen, J. L.; Wang, K. K. Org. Lett. 2006, 8, 4665
35. Zhang, Y.; Petersen, J. L.; Wang, K. K. Org. Lett. 2007, 9, 1025
36. Cinar, M. E.; Vavilala, C.; Fan, J.; Schmittel, M. Org. Biomol. Chem. 2011, 9, 3776
37. Schmittel, M.; Steffen, J.-P.; Wencesla, M. á.; Engels, B.; Lennartz, C.; Hanrath, M. Angew. Chem., Int. Ed. 1998, 37, 1562
38. Schmittel, M.; Rodríguez, D.; Steffen, J.-P. Molecules 2000, 5, 1372
39. Bekele, T.; Christian, C. F.; Lipton, M. A.; Singleton, D. A. J. Am. Chem. Soc. 2005, 127, 9216
40. Samanta, D.; Cinar, M. E.; Das, K.; Schmittel, M. J. Org. Chem. 2013, 78, 1451
41. Carpenter, B. K. J. Am. Chem. Soc. 1985, 107, 5730
42. Carpenter, B. K. Acc. Chem. Res. 1992, 25, 520
43. Fleming, I.; Terrett, N. K. J. Organomet. Chem. 1984, 264, 99
44. Elsevier, C. J.; Stehouwer, P. M.; Westmijze, H.; Vermeer, P. J. Org. Chem. 1983, 48, 1103
45. Frisch, M. J. Gaussian 09, Revision A.1; Gaussian, Wallingford, CT, 2009.
46. Becke, A. D. Phys. Rev. A 1988, 38, 3098
47. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785
48. Ditchfield, R.; Hehre, W. J.; Pople, J. A. J. Chem. Phys. 1971, 54, 724
49. Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257
50. Hariharan, P. C.; Pople, J. A. Theoret. Chim. Acta 1973, 28, 213
51. Prall, M.; Wittkopp, A.; Schreiner, P. R. J. Phys. Chem. A 2001, 105, 9265
52. Zheng, J.; Papajak, E.; Truhlar, D. G. J. Am. Chem. Soc. 2009, 131, 15754
53. Glowacki, D. R.; Liang, C. H.; Marsden, S. P.; Harvey, J. N.; Pilling, M. J. J. Am. Chem. Soc. 2010, 132, 13621
54. Dewar, M. J. S.; Pierini, A. B. J. Am. Chem. Soc. 1984, 106, 203
55. Quijano, L. M. M.; Singleton, D. A. J. Am. Chem. Soc. 2011, 133, 13824
56. Oyola, Y.; Singleton, D. A. J. Am. Chem. Soc. 2009, 131, 3130
57. Andujar-De Sanctis, I. L.; Singleton, D. A. Org. Lett. 2012, 14, 5238
58. Schmittel, M.; von Seggern, H. J. Am. Chem. Soc. 1993, 115, 2165