Peterson olefination: Unexpected rearrangement in the overcrowded polycyclic aromatic ene series

European Journal of Organic Chemistry

Volumn , Issue 33, 2011, Pages 6773-6780

  Assadi, Naela ^a   Pogodin, Sergey ^a   Agranat, Israel ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

Author keywords

Arenes; Density functional calculations; Olefination; Polycycles; Reaction mechanisms; Rearrangement

Indexed keywords

EID: 80855156704     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201100789     Document Type: Article

References (45)

1. Z. Wang, Peterson Olefination, in: Comprehensive Organic Name Reactions and Reagents, Wiley, 2000, vol. 2, chapter 491, pp. 2176-2181.
2. L. Birkofer, O. Stuhl, Top. Curr. Chem. 1980, 88, 33-88.
3. D. J. Ager, Synthesis 1984, 384-398.
4. L. F. van Staden, D. Gravestock, D. J. Ager, Chem. Soc. Rev. 2002, 31, 195-200.
5. N. Kano, T. Kawashima, The Peterson and Related Reactions, in: Modern Carbonyl Olefination (Ed.:, T. Takeda), Wiley-VCH, Weinheim, 2004, chapter 2, pp. 18-103.
6. A. R. Bassindale, R. J. Ellis, P. G. Taylor, Tetrahedron Lett. 1984, 25, 2705-2708.
7. A. R. Bassindale, R. J. Ellis, J. C.-Y. Lau, P. G. Taylor, J. Chem. Soc. Perkin Trans. 2 1986, 593-597.
8. P. F. Hudrlik, D. Peterson, R. J. Rona, J. Org. Chem. 1975, 40, 2263-2264.
9. P. F. Hudrlik, D. Peterson, J. Am. Chem. Soc. 1975, 97, 1464-1468.
10. D. J. Ager, The Peterson Olefination Reaction, in: Organic Reactions, Wiley, New York, 1990, vol. 38, pp. 1-224.
11. G. L. Larson, C. F. de Kaifer, R. Seda, L. E. Torres, J. R. Ramirez, J. Org. Chem. 1984, 49, 3385-3386.
12. T. Kawashima, N. Iwama, R. Okazaki, J. Am. Chem. Soc. 1992, 114, 7598-7599.
13. N. S. Mill, E. E. Burns, J. Hodges, J. Gibbs, E. Esparza, J. L. Malandra, J. Koch, J. Org. Chem. 1998, 63, 3017-3022.
14. A. Levy, A. Rakowitz, N. S. Mills, J. Org. Chem. 2003, 68, 3990-3998.
15. N. S. Mills, M. A. Benish, C. Ybarra, J. Org. Chem. 2002, 67, 2003-2012.
16. P. U. Biedermann, J. J. Stezowski, I. Agranat, in: Advances in Theoretically Interesting Molecules (Ed.:, R. P. Thummel), JAI Press, Stanford, CN, 1998, vol. 4, pp. 245-322.
17. P. U. Biedermann, J. J. Stezowski, I. Agranat, Eur. J. Org. Chem. 2001, 15-34.
18. N. Assadi, S. Pogodin, S. Cohen, A. Levy, I. Agranat, Struct. Chem. 2009, 20, 541-556.
19. D. H. R. Barton, B. J. Wills, J. Chem. Soc. D: Chem. Commun. 1970, 1226-1226.
20. D. H. R. Barton, Reason and Imagination: Reflections on Research, in: Organic Chemistry: Selected Papers of Derek H. R. Barton, Imperial College Press and World Scientific, Singapore, 1996, vol. 6, p. 489.
21. Z. Wang, Barton-Kellogg Olefination, in: Comprehensive Organic Name Reactions and Reagents, Wiley, 2009, vol. 1, chapter 56, pp. 249-253.
22. H. Gilman, R. A. Benkeser, G. E. Dunn, J. Am. Chem. Soc. 1950, 72, 1689-1691.
23. E. D. Bergmann, Bull. Res. Council Isr. 1956, 5a, 150-154.
24. A. Streitwieser Jr., S. M. Brown, J. Org. Chem. 1988, 53, 904-906.
25. A. Levy, M. Goldschmidt, I. Agranat, Lett. Org. Chem. 2006, 3, 579-584.
26. Dictionary of Organic Compounds (Eds.:, J. I. G. Cadogan, S. V. Ley, G. Pattenden, R. A. Raphael, C. W. Rees,), Chapman & Hall, 1996, vol. 1, p. 772.
27. M. Rabinovitz, I. Agranat, A. Weitzen-Dagan, Tetrahedron Lett. 1974, 15, 1241-1244.
28. N. H. Martin, N. W. Allen III, K. D. Moore, L. Vo, THEOCHEM 1998, 454, 161-166.
29. Z. Wang, Haller-Bauer Cleavage, in: Comprehensive Organic Name Reactions and Reagents, Wiley, 2009, vol. 2, chapter 291, p. 1310.
30. G. Mehta, R. V. Venkateswaran, Tetrahedron 2000, 56, 1399-1422.
31. A. Streitwieser Jr., R. G. Lawler, J. Am. Chem. Soc. 1963, 85, 2854-2855.
32. B. N. Papas, S. Wang, N. J. DeYonker, H. L. Woodcock, H. F. Schaefer III, J. Phys. Chem. A 2003, 107, 6311-6316.
33. A. G. Brook, Acc. Chem. Res. 1974, 7, 77-84.
34. Z. Wang, Peterson Olefination, in: Comprehensive Organic Name Reactions and Reagents, Wiley, 2009, vol. 1, chapter 117, pp. 529-535.
35. F. de Proft, P. Geerlings, Chem. Rev. 2001, 101, 1451-1464.
36. W. Koch, M. C. Holthausen, A Chemist's Guide to Density Functional Theory, Wiley-VCH, Weinheim, Germany, 2000.
37. P. U. Biedermann, J. J. Stezowski, I. Agranat, Chem. Commun. 2001, 954-955.
38. S. Pogodin, I. D. Rae, I. Agranat, Eur. J. Org. Chem. 2006, 5059-5068.
39. N. S. Mills, M. Benish, J. Org. Chem. 2006, 71, 2207-2213.
40. S. Pogodin, I. Agranat, J. Org. Chem. 2007, 72, 10096-10107.
41. T. M. Krygowski, M. K. Cyrański, Chem. Rev. 2001, 101, 1385-1419.
42. A. Schönberg, W. I. Awad, N. Latif, J. Chem. Soc. 1951, 1368-1378.
43. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian 03, rev. C.02, Gaussian, Inc., Wallingford CT, 2004.
44. A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652.
45. C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785-789.