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)

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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.
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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.
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