Mechanistic evidence for remote π-aryl participation in acid-catalyzed ring opening of homobenzoquinone epoxides

Chemical Communications

Volumn , Issue 15, 2008, Pages 1804-1806

  Oshima, Takumi ^a   Asahara, Haruyasu ^a   Koizumi, Takuya ^a   Miyamoto, Saki ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACID; BENZOQUINONE DERIVATIVE; BIS(4 CHLOROPHENYL)HOMOBENZOQUINONE EPOXIDE; EPOXIDE; ETHYLENE OXIDE; PHENYL GROUP; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; TOLUENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; PHYSICAL CHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; RING OPENING; X RAY ANALYSIS;

EID: 41549167653     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b719663f     Document Type: Article

References (33)

1. C. J. Lancelot, D. J. Cram and P. v. R. Scheyer, Carbenium Ions, ed., G. A. Olah, and, P. v. R. Scheyer,, Wiley-Interscience, New York, 1972, vol. 3, ch. 27, p. 1347
2. M. B. Smith and J. March, March's Advanced Organic Chemistry, Wiley, New York, 2001, ch. 10, p. 407
3. M. Peeran J. W. Wilt R. Subramanian D. S. Crumrine J. Org. Chem. 1993 58 202
4. D. N. Kevil M. J. D'Souza J. Chem. Soc., Perkin Trans. 2 1997 257
5. M. Fujio N. Goto T. Dairokuno M. Goto Y. Saeki Y. Okusaka Y. Tsuno Bull. Chem. Soc. Jpn. 1992 65 3072
6. S. Nagumo M. Ono Y. Kakimoto T. Furukawa T. Hisano M. Mizukami N. Kawahara H. Akita J. Org. Chem. 2002 67 6618
7. E. del Río M. I. Menéndez R. López T. Sordo J. Am. Chem. Soc. 2001 123 5064
8. N. S. Isaacs, Physical Organic Chemistry, Longman Science & Technical, Essex, 1995, ch. 13, p. 643
9. M. Fujio K. Funatsu M. Goto M. Mishima Y. Tsuno Tetrahedron 1987 43 307
10. M. Fujio M. Goto M. Mishima Y. Tsuno Bull. Chem. Soc. Jpn. 1990 63 1121
11. M. Okamura K. Hazama M. Ohta K. Kato T. Horiguchi Chem. Lett. 1997 26 973
12. Y. Tsuno and M. Fujio, Advances in Physical Organic Chemistry, ed., D. Bethell,, Academic Press, London, 1999, vol. 32, p. 267
13. D. J. Cram J. Am. Chem. Soc. 1952 74 2129
14. D. J. Cram J. Am. Chem. Soc. 1952 74 2137
15. A. Streitwieser, Jr T. D. Walsh J. R. Wolfe J. Am. Chem. Soc. 1965 87 3686
16. D. J. Cram J. A. Thompson J. Am. Chem. Soc. 1967 89 6766
17. J. A. Thompson D. J. Cram J. Am. Chem. Soc. 1969 91 1778
18. L. M. Jackman V. R. Haddon J. Am. Chem. Soc. 1974 96 5130
19. M. Gates D. L. Frank W. C. von Felten J. Am. Chem. Soc. 1974 96 5138
20. T. Ando J. Yamawaki Y. Saito Bull. Chem. Soc. Jpn. 1978 51 219
21. H. Asahara E. Kubo K. Togaya T. Koizumi E. Mochizuki T. Oshima Org. Lett. 2007 9 3421
22. S. M. Hubig J. K. Kochi J. Org. Chem. 2000 65 6807
23. C. Reichardt, Solvents and Solvent Effects in Organic Chemistry, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2003, ch. 5, pp. 147-328
24. C. Reichardt Chem. Rev. 1994 94 2319
25. K. Koizumi K. Harada E. Mochizuki K. Kokubo T. Oshima Org. Lett. 2004 6 4081
26. P. D. Mollere K. N. Houk J. Am. Chem. Soc. 1977 99 3226
27. H. Iwamura T. Sugawara Y. Kawada K. Tori R. Muneyuki R. Noyori Tetrahedron Lett. 1979 20 3449
28. R. D. Bach G. J. Wolber J. Am. Chem. Soc. 1984 106 1410
29. R. E. Parker N. S. Isaacs Chem. Rev. 1959 59 737
30. Y. Kita A. Furukawa J. Futamura K. Higuchi K. Ueda H. Fujioka Tetrahedron 2001 57 815
31. P. Costantino P. Crotti M. Ferretti F. Macchia J. Org. Chem. 1982 47 2917
32. P. Crotti M. Ferretti F. Macchia A. Stoppioni J. Org. Chem. 1984 49 4706
33. P. Crotti M. Ferretti F. Macchia A. Stoppioni J. Org. Chem. 1986 51 2759