Intramolecular anodic carbon-carbon bond formation from oxidized phenol intermediates. Effect of oxygenated substituents on the yields of spiro dienones in electrochemical and iodobenzene diacetate oxidations

Journal of Organic Chemistry

Volumn 61, Issue 4, 1996, Pages 1267-1273

  Swenton, John S ^a   Callinan, Andrew ^a   Chen, Ying ^a   Rohde, Jeffrey J ^a   Kerns, Michael L ^a   Morrow, Gary W ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001616005     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951799d     Document Type: Article

References (45)

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5. For general references concerning the oxidation chemistry of phenols, see the literature cited in ref 1.
6. For recent examples of and leading references to anodic carbon-carbon bond-coupling reactions, see: (a) Maki, S.; Asaba, N.; Kosemuar, S.; Yamamura, S. Tetrahedron Lett. 1992, 33, 4169.
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14. 8 poor yields were obtained. The difference between additions to enones and the work herein is undoubtedly the directive effect of the ether linkages at the 4-position of these quinol ether derivatives.
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24. 3) which would arise from benzylic oxidation of 16c (R = H). However, the compound was not rigorously characterized.
25. The stability of 19e with respect to dimerization is probably related to the steric effect of the 4-aryl substituent. For a discussion, see: Andersson, G.; Bertsson, Acta Chem. Scand., Ser. B 1975, 29, 948. Andersson, G. Ibid. 1976, 30, 64.
26. The stability of 19e with respect to dimerization is probably related to the steric effect of the 4-aryl substituent. For a discussion, see: Andersson, G.; Bertsson, Acta Chem. Scand., Ser. B 1975, 29, 948. Andersson, G. Ibid. 1976, 30, 64.
27. For iodobenzene diacetate oxidation of phenols to quinone monoketals, see: (a) Peiter, A.; Elgendy, S. Tetrahedron Lett. 1988, 29, 677. (b) Tamura, Y.; Yakura, T.; Haruta, J ; Kita, Y. J. Org. Chem. 1987, 52, 3927. (c) Fleck, A. E.; Hobart, J. A.; Morrow, G. W. Synth. Commun. 1992, 22, 179.
28. For iodobenzene diacetate oxidation of phenols to quinone monoketals, see: (a) Peiter, A.; Elgendy, S. Tetrahedron Lett. 1988, 29, 677. (b) Tamura, Y.; Yakura, T.; Haruta, J ; Kita, Y. J. Org. Chem. 1987, 52, 3927. (c) Fleck, A. E.; Hobart, J. A.; Morrow, G. W. Synth. Commun. 1992, 22, 179.
29. For iodobenzene diacetate oxidation of phenols to quinone monoketals, see: (a) Peiter, A.; Elgendy, S. Tetrahedron Lett. 1988, 29, 677. (b) Tamura, Y.; Yakura, T.; Haruta, J ; Kita, Y. J. Org. Chem. 1987, 52, 3927. (c) Fleck, A. E.; Hobart, J. A.; Morrow, G. W. Synth. Commun. 1992, 22, 179.
30. For phenolic coupling reactions with positive iodine reagents, see: Szantay, C.; Blasko, G.; Barczai-Beke, Pechy, P.; Dornyei, G. Tetrahedron Lett. 1980, 21, 3509. Rama Krishna, K. V.; Sujatha, K.; Kapil, R. S. Ibid. 1990, 31, 1351. Kita, Y.; Yakura, T.; Tohma, H.; Kikuchi, K. Tetrahedron Lett. 1989, 30, 1119.
31. For phenolic coupling reactions with positive iodine reagents, see: Szantay, C.; Blasko, G.; Barczai-Beke, Pechy, P.; Dornyei, G. Tetrahedron Lett. 1980, 21, 3509. Rama Krishna, K. V.; Sujatha, K.; Kapil, R. S. Ibid. 1990, 31, 1351. Kita, Y.; Yakura, T.; Tohma, H.; Kikuchi, K. Tetrahedron Lett. 1989, 30, 1119.
32. For phenolic coupling reactions with positive iodine reagents, see: Szantay, C.; Blasko, G.; Barczai-Beke, Pechy, P.; Dornyei, G. Tetrahedron Lett. 1980, 21, 3509. Rama Krishna, K. V.; Sujatha, K.; Kapil, R. S. Ibid. 1990, 31, 1351. Kita, Y.; Yakura, T.; Tohma, H.; Kikuchi, K. Tetrahedron Lett. 1989, 30, 1119.
33. For nonoxidative methods for generating phenoxonium ions, see: Mortlock, S. V.; Seckington, J. K.; Thomas, E. J. J. Chem. Soc., Perkin Trans. 1988, 2305. Abramovitch, R. A.; Alvernhe, G., Bartnik, R.; Dassanayake, N. L.; Inbasekaran, M. N.; Kato, S. J. Am. Chem. Soc. 1981, 103, 4558. Shudo, K.; Orihara, Y.; Ohta, T.; Okamota, T. J. Am. Chem. Soc. 1981, 103, 943 and references cited therein
34. For nonoxidative methods for generating phenoxonium ions, see: Mortlock, S. V.; Seckington, J. K.; Thomas, E. J. J. Chem. Soc., Perkin Trans. 1988, 2305. Abramovitch, R. A.; Alvernhe, G., Bartnik, R.; Dassanayake, N. L.; Inbasekaran, M. N.; Kato, S. J. Am. Chem. Soc. 1981, 103, 4558. Shudo, K.; Orihara, Y.; Ohta, T.; Okamota, T. J. Am. Chem. Soc. 1981, 103, 943 and references cited therein
35. For nonoxidative methods for generating phenoxonium ions, see: Mortlock, S. V.; Seckington, J. K.; Thomas, E. J. J. Chem. Soc., Perkin Trans. 1988, 2305. Abramovitch, R. A.; Alvernhe, G., Bartnik, R.; Dassanayake, N. L.; Inbasekaran, M. N.; Kato, S. J. Am. Chem. Soc. 1981, 103, 4558. Shudo, K.; Orihara, Y.; Ohta, T.; Okamota, T. J. Am. Chem. Soc. 1981, 103, 943 and references cited therein
36. For extensions of these model studies to bimolecular anodic carbon-carbon bond formation via phenol oxidations, see: (a) Wang, S.; Gates, B. D.; Swenton, J. S. J. Org. Chem. 1991, 56, 1979. (b) Gates, B. D., Dalidowicz, P.; Tebben, A.; Wang, S.; Swenton, J. S. Ibid. 1992, 57, 1992. (c) Kerns, M. L.; Conroy, S. M.; Swenton, J. S. Tetrahedron Lett. 1994, 35, 7529.
37. For extensions of these model studies to bimolecular anodic carbon-carbon bond formation via phenol oxidations, see: (a) Wang, S.; Gates, B. D.; Swenton, J. S. J. Org. Chem. 1991, 56, 1979. (b) Gates, B. D., Dalidowicz, P.; Tebben, A.; Wang, S.; Swenton, J. S. Ibid. 1992, 57, 1992. (c) Kerns, M. L.; Conroy, S. M.; Swenton, J. S. Tetrahedron Lett. 1994, 35, 7529.
38. For extensions of these model studies to bimolecular anodic carbon-carbon bond formation via phenol oxidations, see: (a) Wang, S.; Gates, B. D.; Swenton, J. S. J. Org. Chem. 1991, 56, 1979. (b) Gates, B. D., Dalidowicz, P.; Tebben, A.; Wang, S.; Swenton, J. S. Ibid. 1992, 57, 1992. (c) Kerns, M. L.; Conroy, S. M.; Swenton, J. S. Tetrahedron Lett. 1994, 35, 7529.
39. (a) Wang, S., Morrow, G. W.; Swenton, J S. J. Org. Chem. 1989, 54, 5364. See also ref 20
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