Photochemical and acid-catalyzed rearrangements of 4-carbomethoxy-4-methyl-3-(trimethylsilyl)-2,5-cyclohexadien-1-one

Journal of Organic Chemistry

Volumn 61, Issue 14, 1996, Pages 4555-4559

  Schultz, Arthur G ^a   Antoulinakis, Evan G ^a  

^a RENSSELAER POLYTECHNIC INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001658310     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo952240g     Document Type: Article

References (40)

1. (a) Zimmerman, H. E.; Schuster, D. I. J. Am. Chem. Soc. 1962, 84, 4527-4540.
2. (b) Schultz, A. G. Rearrangement Reactions of Cross-Conjugated Cyclohexadienones. In CRC Handbook of Organic Photochemistry and Photobiology; Horspool, W. M., Song, P.-S., Eds.; CRC Press: London, 1995; pp 685-700.
3. (a) Marx, J. N.; Argyle, J. C.; Norman, L. R. J. Am. Chem. Soc. 1974, 96, 2121-2129.
4. (b) Marx, J. N.; Bombach, E. J. Tetrahedron Lett. 1977, 18, 2391-2394.
5. (c) Vitullo, V. P.; Cashen, M. J.; Marx, J. N.; Candle, L. J.; Fritz, J. R. J. Am. Chem. Soc. 1978, 100, 1205-1210.
6. (d) Schultz, A. G.; Harrington, R. E.; Macielag, M.; Mehta, P. G.; Taveras, A. G. J. Org. Chem. 1987, 52, 5482-5484.
7. (e) Marx, J. N.; Hahn, Y.-S. P. J. Org. Chem. 1988, 53, 2866-2868.
8. (f) Schultz, A. G.; Hardinger, S. A. J. Org. Chem. 1991, 56, 1105-1111.
9. (g) Marx, J. N.; Zuerker, J.; Hahn, Y.-S. P. Tetrahedron Lett. 1991, 32, 1921-1924.
10. For reviews of the dienone-phenol rearrangement, see: (a) de Mayo, P. In Elucidation of Structures by Physical and Chemical Methods; Bentley, K. W., Ed.; Wiley-Interscience: New York, 1963; p 1106. (b) Collins, C. J.; Eastham, J. F. In The Chemistry of the Carbonyl Group; Patai, S., Ed.; Wiley-Interscience: New York, 1966; p 775. (c) Waring, A. J. Adv. Alicycl. Chem. 1966, 1, 207. (d) Miller, B. In Mechanisms of Molecular Migrations; Thyagarajan, B. S., Ed.; Wiley-Interscience: New York, 1969; Vol. 1, p 275.
11. For reviews of the dienone-phenol rearrangement, see: (a) de Mayo, P. In Elucidation of Structures by Physical and Chemical Methods; Bentley, K. W., Ed.; Wiley-Interscience: New York, 1963; p 1106. (b) Collins, C. J.; Eastham, J. F. In The Chemistry of the Carbonyl Group; Patai, S., Ed.; Wiley-Interscience: New York, 1966; p 775. (c) Waring, A. J. Adv. Alicycl. Chem. 1966, 1, 207. (d) Miller, B. In Mechanisms of Molecular Migrations; Thyagarajan, B. S., Ed.; Wiley-Interscience: New York, 1969; Vol. 1, p 275.
12. For reviews of the dienone-phenol rearrangement, see: (a) de Mayo, P. In Elucidation of Structures by Physical and Chemical Methods; Bentley, K. W., Ed.; Wiley-Interscience: New York, 1963; p 1106. (b) Collins, C. J.; Eastham, J. F. In The Chemistry of the Carbonyl Group; Patai, S., Ed.; Wiley-Interscience: New York, 1966; p 775. (c) Waring, A. J. Adv. Alicycl. Chem. 1966, 1, 207. (d) Miller, B. In Mechanisms of Molecular Migrations; Thyagarajan, B. S., Ed.; Wiley-Interscience: New York, 1969; Vol. 1, p 275.
13. For reviews of the dienone-phenol rearrangement, see: (a) de Mayo, P. In Elucidation of Structures by Physical and Chemical Methods; Bentley, K. W., Ed.; Wiley-Interscience: New York, 1963; p 1106. (b) Collins, C. J.; Eastham, J. F. In The Chemistry of the Carbonyl Group; Patai, S., Ed.; Wiley-Interscience: New York, 1966; p 775. (c) Waring, A. J. Adv. Alicycl. Chem. 1966, 1, 207. (d) Miller, B. In Mechanisms of Molecular Migrations; Thyagarajan, B. S., Ed.; Wiley-Interscience: New York, 1969; Vol. 1, p 275.
14. (a) Gilman, H.; Arntzen, C. E. J. Am. Chem. Soc. 1947, 69, 1537-1538.
15. (b) Benkeser, R. A.; Krysiak, H. R. J. Am. Chem. Soc. 1954, 76, 599-603.
16. (c) Parham, W. E.; Sayed, Y. A. J. Org. Chem. 1974, 39, 2051-2033.
17. Mills, R. J.; Taylor, N. J.; Snieckus, V. J. Org. Chem. 1989, 54, 4372-4385.
18. (a) Krizan, T. D.; Martin, J. C. J. Am. Chem. Soc. 1983, 105, 6155-6157.
19. (b) Severson, R. G.; Rosscup, R. J. J. Am. Chem. Soc. 1954, 76, 4552-4554.
20. (c) Earborn, E.; Walton, D. R. M.; Young, D. J. J. Chem. Soc. (B) 1989, 15-20.
21. (d) Nietzschmann, E.; Tzschach, A.; Duchek, I.; Heinicke, J.; Thust, U.; Kemter, P. Ger. (East) DD 268,697; Chem. Abstr. 1990, 112, 77534r.
22. (e) The methyl ester: Jung, M. E.; Gaede, B. Tetrahedron Lett. 1979, 35, 621-625.
23. (f) The tert-butyl ester: Boybin, D. W. Ph.D. Dissertation, Duke University, 1978.
24. Comins, D. L.; Brown, J. D. J. Org. Chem. 1984, 49, 1078-1083.
25. This oxidation was first performed by Aihua Wang, RPI Laboratories.
26. (a) Referenced as: R. Urech, personal communication in Hook, J. M.; Mander, L. N. Nat. Prod. Rep. 1986, 3, 35-85.
27. (b) Rabideau, P. W.; Marcinow, Z. Org. Reactions 1992, 42, 1-334.
28. Colvin, E. Silicon in Organic Synthesis; Butterworths: London, 1981.
29. (a) Schultz, A. G. Acc. Chem. Res. 1990, 23, 207-213.
30. (b) Schultz, A. G. J. Chinese Chem. Soc. (Taiwan) 1994, 41, 487-495.
31. Schultz, A. G.; Lavieri, F. P.; Macielag, M.; Plummer, M. J. Am. Chem. Soc. 1987, 109, 3991-4000.
32. Schultz, A. G.; Reilly, J. J. Am. Chem. Soc. 1992, 114, 5068-5073.
33. Zimmerman, H. E.; Keese, R.; Nasielski, J.; Swenton, J. S. J. Am. Chem. Soc. 1966, 88, 4895-4904.
34. Zimmerman, H. E.; Epling, G. A. J. Am. Chem. Soc. 1972, 94, 7806-7811.
35. 3Si (-0.07); see: Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165-195.
36. (b) To the extent that the intermediate in the type B photorearrangement might be represented as a biradicaloid, it should be noted that the trimethylsilyl group has been found to exert a small destabilizing effect on adjacent radicals; see: Zhang, S.; Zhang, X.-M.; Bordwell, F. G. J. Am. Chem. Soc. 1995, 117, 602-606.
37. Griffiths, J.; Hart, H. J. Am. Chem. Soc. 1968, 90, 5296-5298.
38. Schultz, A. G.; Green, N. J. J. Am. Chem. Soc. 1992, 114, 1824-1829.
39. For previous preparations of 21, see: Phandis, A. P.; Nanda, B.; Sarita, A.; Patwardhan, E.; Gupta, A. S. Indian J. Chem. 1984, 23B, 1098 and ref 2d.
40. Danheiser, R. L.; Sard, H. J. Org. Chem. 1980, 45, 4810-4812.