Diels-Alder reactions of allene with benzene and butadiene: Concerted, stepwise, and ambimodal transition states

Journal of Organic Chemistry

Volumn 79, Issue 19, 2014, Pages 8968-8976

  Pham, Hung V ^a   Houk, K N ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; BUTADIENE; CYCLOADDITION; POTENTIAL ENERGY; QUANTUM CHEMISTRY; REACTION INTERMEDIATES;

COMPLETE ACTIVE SPACE; CONCERTED MECHANISM; CYCLOADDITIONS; DIELS-ALDER REACTION; DIENOPHILES; DIRADICAL INTERMEDIATES; RADICAL PATHWAY; TRANSITION STATE;

SURFACE REACTIONS;

1,3 BUTADIENE; ALLENE DERIVATIVE; BENZENE; RADICAL; 1,3 BUTADIENE DERIVATIVE; 1,3-BUTADIENE; ALKADIENE; PROPADIENE;

ARTICLE; CONFORMATION; COPE REARRANGEMENT; CYCLOADDITION; DIELS ALDER REACTION; DIMERIZATION; MOLECULAR DYNAMICS; REACTION ANALYSIS; REACTION TIME; RING OPENING; STEREOCHEMISTRY; STEREOISOMERISM; CHEMISTRY; COMPUTER SIMULATION;

ALKADIENES; BENZENE; BUTADIENES; COMPUTER SIMULATION; CYCLOADDITION REACTION;

EID: 84907783190     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo502041f     Document Type: Article

References (58)

1. Krause, N.; Hashimi, A. S. K. Modern Allene Chemistry; Wiley-VCH Verlag: Weinheim, 2004; Vols. 1-2.
2. Diels, O.; Alder, K. Justus Liebigs Ann. Chem. 1926, 450, 237-254
3. Fringuelli, F.; Taticchi, A. Dienes in the Diels-Alder Reaction; Wiley & Sons: New York, 1990.
4. Ciganek, E. Tetrahedron Lett. 1967, 8, 3321-3325
5. Cossu, S.; Garris, F.; DeLucchi, O. Synlett 1997, 12, 1327-1334
6. Yu, S.; Ma, S. Angew. Chem., Int. Ed. 2012, 51, 3074-3112
7. Jensen, F. J. Am. Chem. Soc. 1995, 117, 7487-7492
8. Wentrup, C.; Finnerty, J. J.; Koch, R. Curr. Org. Chem. 2010, 14, 1586-1599
9. Sakai, S. J. Phys. Chem. A 2006, 110, 9443-9450
10. Sakai, S. Theor. Chem. Acc. 2008, 120, 177-183
11. Inagaki, F.; Kitagaki, S.; Mukai, C. Syn. Lett. 2011, 5, 594-614
12. Black, K. A.; Wilsey, S.; Houk, K. N. J. Am. Chem. Soc. 1998, 120, 5622-5627
13. Scheufler, F.; Maier, M. E. Eur. J. Org. Chem. 2000, 3945-3948
14. Padwa, A.; Kline, D. N.; Koehler, K. F.; Matzinger, M.; Venkatramanan, M. K. J. Org. Chem. 1987, 52, 3909-3917
15. For a review on allene dipolarophiles, see: Pinho e Melo, T. M. V. D. Curr. Org. Chem. 2009, 13, 1406-1431
16. Lebedev, S. V. J. Russ. Phys. Chem. Soc. 1913, 45, 1357-1372
17. Dai, S.-H.; Dolbier, W. R., Jr. J. Org. Chem. 1972, 37, 950-955
18. Kavitha, K.; Venuvanalingam, P. J. Chem. Soc., Perkin Trans. 2 2002, 2130-2139
19. Mariappan, M.; Venuvanalingam J. Fluorine Chem. 1994, 73, 171-174
20. Skraba, S. L.; Johnson, R. P. J. Org. Chem. 2012, 77, 11096-11100
21. Mariappan, M.; Venuvanalingam, P. J. Chem. Soc., Perkin Trans. 2 1996, 1423-1427
22. Rastelli, A.; Bagatti, M.; Gandolfi, R. J. Am. Chem. Soc. 1995, 117, 4965-4975
23. Nendel, M.; Tolbert, L. M.; Herring, L. E.; Islam, N.; Houk, K. N. J. Org. Chem. 1999, 64, 976-983
24. Froese, R. D. J.; Coxon, J. M.; West, S. C.; Morokuma, K. J. Org. Chem. 1997, 62, 6991-6996
25. Houk, K. N.; Li, Y.; Evanseck, J. D. Angew. Chem., Int. Ed. Engl. 1992, 31, 682-708
26. Coxon, J. M.; Grice, S. T.; Maclagan, R. G. A. R.; McDonald, D. Q. J. Org. Chem. 1990, 55, 3804
27. González, J.; Houk, K. N. J. Org. Chem. 1992, 57, 3031-3037
28. Yoshino, T.; Ng, F.; Danishefsky, S. J. J. Am. Chem. Soc. 2006, 128, 14185-14191
29. Jung, M. E.; Novack, A. R. Tetrahedron Lett. 2005, 46, 8237-8240
30. Jung, M. E.; Nishimura, N.; Novack, A. J. Am. Chem. Soc. 2005, 127, 11206-11207
31. Jung, M. E.; Nishimura, N. Org. Lett. 2001, 3, 2113-2116
32. Zhao, Y.-L.; Suhrada, C. P.; Jung, M. E.; Houk, K. N. J. Am. Chem. Soc. 2006, 128, 11106-11113
33. Himbert, G.; Henn, L. Angew. Chem., Int. Ed. 1982, 21, 620
34. Lam, J. K.; Schmidt, Y.; Vanderwal, C. D. Org. Lett. 2012, 14, 5566-5569
35. Schmidt, Y.; Lam, J. K.; Pham, H. V.; Houk, K. N.; Vanderwal, C. D. J. Am. Chem. Soc. 2013, 135, 7339-7348
36. Roos, B. O. In Advances in Chemical Physics; John Wiley & Sons, Inc.: New York, 2007; p 399.
37. Frisch, M. J.; Gaussian 09, revision C.01; Gaussian, Inc.: Wallingford, CT, 2009.
38. Andersson, K.; Malmqvist, P. A.; Roos, B. O.; Sadlej, A. J.; Wolinski, K. J. Phys. Chem. 1990, 94, 5483-5488
39. Aquilante, F.; De Vico, L.; Ferré, N.; Ghigo, G.; Malmqvist, P.-Å; Neogrády, P.; Pedersen, T. B.; Pitonak, M.; Reiher, M.; Roos, B. O.; Serrano-Andrés, L.; Urban, M.; Veryazov, V.; Lindh, R. J. Comput. Chem. 2010, 31, 224-227
40. Ess, D. H.; Hayden, A. E.; Klärner, F.-G.; Houk, K. N. J. Org. Chem. 2008, 73, 7586-7592.
41. Li, Y.; Houk, K. N. J. Am. Chem. Soc. 1996, 118, 880-885
42. Houk, K. N.; Li, Y.; Storer, J.; Raimondi, L.; Beno, B. J. Chem. Soc., Faraday Trans. 1994, 90, 1599-1604
43. Zhao, Y.-L.; Suhrada, C. P.; Jung, M. E.; Houk, K. N. J. Am. Chem. Soc. 2006, 128, 11106-11113
44. Northrop, B. H.; Houk, K. N. J. Org. Chem. 2005, 71, 3-13
45. Barborini, M.; Guidoni, L. J. Chem. Phys. 2012, 137, 224309-224309-9 and references cited therein
46. Ess, D. H.; Wheeler, S. E.; Iafe, R. G.; Xu, L.; Çelebi-Ölçüm, N.; Houk, K. N. Angew. Chem., Int. Ed. 2008, 47, 7592-7601
47. Thomas, J. B.; Waas, J. R.; Harmata, M.; Singleton, D. A. J. Am. Chem. Soc. 2008, 130, 14544-14555
48. Gonzalez-James, O. M.; Kwan, E. E.; Singleton, D. A. J. Am. Chem. Soc. 2012, 134, 1914-1917
49. Ussing, B. R.; Hang, C.; Singleton, D. A. J. Am. Chem. Soc. 2006, 128, 7594-7607
50. Bekele, T.; Christian, C. F.; Lipton, M. A.; Singleton, D. A. J. Am. Chem. Soc. 2005, 127, 9216-9223
51. Hrovat, D. A.; Duncan, J. A.; Borden, W. T. J. Am. Chem. Soc. 1999, 121, 169-175
52. Ammal, S. C.; Yamataka, H.; Aida, M.; Dupuis, M. Science 2003, 299, 1555-1557
53. Dolbier, W. R.; Dai, S.-H. J. Am. Chem. Soc. 1970, 92, 1774-1776
54. Trifonov, L. S.; Orahovats, A. S. Helv. Chim. Acta 1989, 72, 59-64
55. Trifonov, L. S.; Orahovats, A. S. Helv. Chim. Acta 1987, 70, 262-270
56. Baker, J.; Scheiner, A.; Andzelm, J. Chem. Phys. Lett. 1993, 216, 380-388
57. Black, K.; Liu, P.; Xu, L.; Doubleday, C.; Houk, K. N. Proc. Natl. Acad. Sci. U.S.A. 2012, 109, 12860-12865
58. Doering, W. v. E.; Roth, W. R.; Breuckmann, R.; Figge, L.; Lennartz, H.-W.; Fessner, W.-D.; Prinzbach, H. Chem. Ber. 1988, 121, 1-9 and references cited therein