Dienone tautomers of 4-alkoxy-2,6-di-terf-butylphenols

Journal of Organic Chemistry

Volumn 61, Issue 20, 1996, Pages 7156-7161

  Omura, Kanji ^a  

^a KOSHIEN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1842351351     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9609945     Document Type: Article

References (53)

1. (1)(a) Lasne, M.-C.; Ripoll, J.-L.; Denis, J.-M. Tetrahedron Lett. 1980, 21, 463.
2. (b) Capponi, M.; Gut, I.; Wirz, J. Angew. Chem., Int. Ed. Engl. 1986, 25, 344.
3. (a) Ershov, V. V.; Volod'kin, A. A. Izv. Mad. Nauk SSSR, Otd. Khim, Nauk 1962, 730.
4. (b) Volod'kin, A. A.; Ershov, V. V. Izv. Akad. Nauk SSSR, Otd. Khim. Nauk 1962, 2022.
5. (c) Fyfe, C. A.; Van Veen, L., Jr. J. Am. Chem. Soc. 1977, 99, 3366.
6. (d) Pearson, D. E.; Venkataramu, S. D.; Childers, W. E., Jr. Synth. Commun. 1979, 9, 5.
7. (e) Baciocchi, E.; Bocca, P. L. Ric. Sci. 1969, 39, 68.
8. (a) Kharasch, M. S.; Joshi, B. S. J. Org. Chem. 1957, 22, 1439.
9. (b) Ley, K; Müller, E.; Mayer, R.; Scheffler, K. Chem Ber. 1958, 91, 2670.
10. (c) Omura, K. J. Org. Chem. 1991, 56, 921.
11. Matsuura, T.; Ogura, K. J. Am. Chem. Soc. 1967, 89, 3846.
12. For specifically substituted phenols including hydroxy derivatives of polycondensed aromatic hydrocarbons, the tautomeric cyclohexadienone forms of type 1a or 1b are known, which are isolable in the individual state or exist in an appropriate solvent. Some of these dienone forms are energetically favored over the phenol forms, and in limited cases only the dienone forms are known. The actual cyclohexadienone-phenol tautomerism, as a mobile equilibrium, has been rarely observed experimentally. See: (a) Ershov, V. V.; Nikiforov, G. A. Russ. Chem. Rev. 1966, 35, 817. (b) Forsén, S.; Nilsson, M. In The Chemistry of the Carbonyl Group; Patai, S., Ed.; Wiley: New York, 1970; Vol. 2, p 157. (c) Crozier, R. F.; Hewitt, D. G. Aust. J. Chem. 1972, 25, 183. (d) Highet, R. J.; Chou, F. E. J. Am. Chem. Soc. 1977, 99, 3538. (e) Teuber, H.-J.; Götz, N. Chem. Ber. 1956, 89, 2654. (f) Teuber, H.-J.; Thaler, G. Chem. Ber. 1959, 92, 667.
13. For specifically substituted phenols including hydroxy derivatives of polycondensed aromatic hydrocarbons, the tautomeric cyclohexadienone forms of type 1a or 1b are known, which are isolable in the individual state or exist in an appropriate solvent. Some of these dienone forms are energetically favored over the phenol forms, and in limited cases only the dienone forms are known. The actual cyclohexadienone-phenol tautomerism, as a mobile equilibrium, has been rarely observed experimentally. See: (a) Ershov, V. V.; Nikiforov, G. A. Russ. Chem. Rev. 1966, 35, 817. (b) Forsén, S.; Nilsson, M. In The Chemistry of the Carbonyl Group; Patai, S., Ed.; Wiley: New York, 1970; Vol. 2, p 157. (c) Crozier, R. F.; Hewitt, D. G. Aust. J. Chem. 1972, 25, 183. (d) Highet, R. J.; Chou, F. E. J. Am. Chem. Soc. 1977, 99, 3538. (e) Teuber, H.-J.; Götz, N. Chem. Ber. 1956, 89, 2654. (f) Teuber, H.-J.; Thaler, G. Chem. Ber. 1959, 92, 667.
14. For specifically substituted phenols including hydroxy derivatives of polycondensed aromatic hydrocarbons, the tautomeric cyclohexadienone forms of type 1a or 1b are known, which are isolable in the individual state or exist in an appropriate solvent. Some of these dienone forms are energetically favored over the phenol forms, and in limited cases only the dienone forms are known. The actual cyclohexadienone-phenol tautomerism, as a mobile equilibrium, has been rarely observed experimentally. See: (a) Ershov, V. V.; Nikiforov, G. A. Russ. Chem. Rev. 1966, 35, 817. (b) Forsén, S.; Nilsson, M. In The Chemistry of the Carbonyl Group; Patai, S., Ed.; Wiley: New York, 1970; Vol. 2, p 157. (c) Crozier, R. F.; Hewitt, D. G. Aust. J. Chem. 1972, 25, 183. (d) Highet, R. J.; Chou, F. E. J. Am. Chem. Soc. 1977, 99, 3538. (e) Teuber, H.-J.; Götz, N. Chem. Ber. 1956, 89, 2654. (f) Teuber, H.-J.; Thaler, G. Chem. Ber. 1959, 92, 667.
15. For specifically substituted phenols including hydroxy derivatives of polycondensed aromatic hydrocarbons, the tautomeric cyclohexadienone forms of type 1a or 1b are known, which are isolable in the individual state or exist in an appropriate solvent. Some of these dienone forms are energetically favored over the phenol forms, and in limited cases only the dienone forms are known. The actual cyclohexadienone-phenol tautomerism, as a mobile equilibrium, has been rarely observed experimentally. See: (a) Ershov, V. V.; Nikiforov, G. A. Russ. Chem. Rev. 1966, 35, 817. (b) Forsén, S.; Nilsson, M. In The Chemistry of the Carbonyl Group; Patai, S., Ed.; Wiley: New York, 1970; Vol. 2, p 157. (c) Crozier, R. F.; Hewitt, D. G. Aust. J. Chem. 1972, 25, 183. (d) Highet, R. J.; Chou, F. E. J. Am. Chem. Soc. 1977, 99, 3538. (e) Teuber, H.-J.; Götz, N. Chem. Ber. 1956, 89, 2654. (f) Teuber, H.-J.; Thaler, G. Chem. Ber. 1959, 92, 667.
16. For specifically substituted phenols including hydroxy derivatives of polycondensed aromatic hydrocarbons, the tautomeric cyclohexadienone forms of type 1a or 1b are known, which are isolable in the individual state or exist in an appropriate solvent. Some of these dienone forms are energetically favored over the phenol forms, and in limited cases only the dienone forms are known. The actual cyclohexadienone-phenol tautomerism, as a mobile equilibrium, has been rarely observed experimentally. See: (a) Ershov, V. V.; Nikiforov, G. A. Russ. Chem. Rev. 1966, 35, 817. (b) Forsén, S.; Nilsson, M. In The Chemistry of the Carbonyl Group; Patai, S., Ed.; Wiley: New York, 1970; Vol. 2, p 157. (c) Crozier, R. F.; Hewitt, D. G. Aust. J. Chem. 1972, 25, 183. (d) Highet, R. J.; Chou, F. E. J. Am. Chem. Soc. 1977, 99, 3538. (e) Teuber, H.-J.; Götz, N. Chem. Ber. 1956, 89, 2654. (f) Teuber, H.-J.; Thaler, G. Chem. Ber. 1959, 92, 667.
17. For specifically substituted phenols including hydroxy derivatives of polycondensed aromatic hydrocarbons, the tautomeric cyclohexadienone forms of type 1a or 1b are known, which are isolable in the individual state or exist in an appropriate solvent. Some of these dienone forms are energetically favored over the phenol forms, and in limited cases only the dienone forms are known. The actual cyclohexadienone-phenol tautomerism, as a mobile equilibrium, has been rarely observed experimentally. See: (a) Ershov, V. V.; Nikiforov, G. A. Russ. Chem. Rev. 1966, 35, 817. (b) Forsén, S.; Nilsson, M. In The Chemistry of the Carbonyl Group; Patai, S., Ed.; Wiley: New York, 1970; Vol. 2, p 157. (c) Crozier, R. F.; Hewitt, D. G. Aust. J. Chem. 1972, 25, 183. (d) Highet, R. J.; Chou, F. E. J. Am. Chem. Soc. 1977, 99, 3538. (e) Teuber, H.-J.; Götz, N. Chem. Ber. 1956, 89, 2654. (f) Teuber, H.-J.; Thaler, G. Chem. Ber. 1959, 92, 667.
18. (a) Chambers, R. D.; Goggin, P.; Musgrave, W. K. R. J. Chem. Soc. 1959, 1804.
19. (b) McClure, J. D. J. Org. Chem. 1963, 28, 69.
20. (a) Pfoertner, K.; Böse, D. Helv. Chim. Acta 1970, 53, 1553.
21. (b) van Dort, H. M.; Geursen, H. J. Recueil 1967, 86, 520.
22. (c) Armstrong, D. R; Breckenridge, R. J.; Cameron, C.; Nonhebel, D. C.; Pauson, P. L.; Perkins, P. G. Tetrahedron Lett. 1983, 24, 1071.
23. (d) Ngo, M.; Larson, K. R.; Mendenhall, G. D. J. Org. Chem. 1986, 51, 5390.
24. (a) Ronlán, A. J. Chem. Soc. D 1971, 1643.
25. (b) Nilsson, A.; Palmquist, U.; Pettersson, T.; Ronlán, A. J. Chem. Soc., Perkin Trans. 1 1978, 696.
26. (c) Endo, Y.; Shudo, K. Yakugaku Zasshi 1994, 114, 565.
27. (d) Pelter, A.; Elgendy, S. M. A. J. Chem. Soc., Perkin Trans. 1 1993, 1891.
28. (e) Mckillop, A.; Perry, D. H.; Edwards, M. J. Org. Chem. 1976, 41, 282.
29. Ronlán, A.; Parker, V. D. J. Chem. Soc. C 1971, 3214.
30. 2 was assumed to be quantitative.
31. 2 in MeOH. See: Omura, K. J. Org. Chem. 1996, 61, 2006.
32. 1H NMR spectroscopy. After 3 min about one-half of the 3b was found to survive, and after 25 min only singlets due to 7 were observed.
33. Coppinger, G. M.; Campbell, T. W. J. Am. Chem. Soc. 1953, 75, 734.
34. (a) Müller, E.; Ley, K.; Kiedaisch, W. Chem. Ber. 1954, 87, 1605.
35. (b) Tashiro, M.; Fukata, G.; Yoshiya, H. Synthesis 1979, 988.
36. The spectral properties of cyclohexadienones have been described in detail. See: (a) Rieker, A.; Rundel, W.; Kessler, H. Z. Naturforsch 1969, 24b, 547. (b) Rieker, A.; Berger, S. Org. Magn. Reson. 1972, 4, 857.
37. The spectral properties of cyclohexadienones have been described in detail. See: (a) Rieker, A.; Rundel, W.; Kessler, H. Z. Naturforsch 1969, 24b, 547. (b) Rieker, A.; Berger, S. Org. Magn. Reson. 1972, 4, 857.
38. 4 (see Experimental Section).
39. 2 anion concertedly and free cation 8 accordingly is not generated.
40. 3) gave rise to 10a and 10d in 76% and 14% yields, respectively, after chromatography of the crude product.
41. In the reaction with t-BuOH, DME was employed as a cosolvent to avoid freezing (see Experimental Section).
42. 4, giving 14 quantitatively.
43. (a) Galli, C. J. Org. Chem. 1991, 56, 3238.
44. (b) Derbyshire, D. H.; Waters, W. A. J. Chem. Soc. 1950, 3694.
45. (c) Myhre, P. C.; Owen, G. S.; James, L. L. J. Am Chem. Soc. 1968, 90, 2115.
46. (d) Sy, W.-W. Synth. Commun. 1992, 22, 3215.
47. Becker, H.-D.; Gustafsson, K. J. Org. Chem. 1979, 44, 428.
48. Müller, E.; Ley, K. Chem. Ber. 1955, 88, 601.
49. Cook, C. D.; Kuhn, D. A.; Fianu, P. J. Am. Chem. Soc. 1956, 78, 2002.
50. Plekhanova, L. G.; Nikiforov, G. A.; Ershov, V. V. Izv. Akad. Nauk SSSR, Ser. Khim. 1969, 961.
51. Cook, C. D.; Woodworth, R. C.; Fianu, P. J. Am. Chem. Soc. 1956, 78, 4159.
52. Omura, K. J. Org. Chem. 1989, 54, 1987.
53. Müller, E.; Rieker, A.; Mayer, R.; Scheffler, K. Justus Liebigs Ann. Chem. 1961, 645, 36.