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Volumn 61, Issue 4, 1996, Pages 1459-1466

Unexpected oxadi-π-methane rearrangement of β,γ-unsaturated aldehydes

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EID: 0000262570     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951032l     Document Type: Article
Times cited : (21)

References (47)
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    • (1966) Photochemistry
    • Calvert, G.J.1    Pitts, J.N.2
  • 2
    • 0004344770 scopus 로고
    • Benjamin Cummings Publishing Co.: Menlo Park, CA
    • For example, see: (a) Calvert, G. J.; Pitts, J. N. Photochemistry, John Wiley: New York, 1966. (b) Turro, N. J. Modern Molecular Photochemistry; Benjamin Cummings Publishing Co.: Menlo Park, CA, 1978. (c) Horspool, W. M.; Armesto, D. Organic Photochemistry; Ellis Horwood and PTR Prentice Hall: Chichester, England, 1992. (d) CRC Handbook of Organic Photochemistry and Photobiology; Horspool, W. M., Song, P., Ed.; CRC Press: Boca Raton, FL, 1995.
    • (1978) Modern Molecular Photochemistry
    • Turro, N.J.1
  • 3
    • 0004105590 scopus 로고
    • Ellis Horwood and PTR Prentice Hall: Chichester, England
    • For example, see: (a) Calvert, G. J.; Pitts, J. N. Photochemistry, John Wiley: New York, 1966. (b) Turro, N. J. Modern Molecular Photochemistry; Benjamin Cummings Publishing Co.: Menlo Park, CA, 1978. (c) Horspool, W. M.; Armesto, D. Organic Photochemistry; Ellis Horwood and PTR Prentice Hall: Chichester, England, 1992. (d) CRC Handbook of Organic Photochemistry and Photobiology; Horspool, W. M., Song, P., Ed.; CRC Press: Boca Raton, FL, 1995.
    • (1992) Organic Photochemistry
    • Horspool, W.M.1    Armesto, D.2
  • 4
    • 85028579626 scopus 로고
    • CRC Press: Boca Raton, FL
    • For example, see: (a) Calvert, G. J.; Pitts, J. N. Photochemistry, John Wiley: New York, 1966. (b) Turro, N. J. Modern Molecular Photochemistry; Benjamin Cummings Publishing Co.: Menlo Park, CA, 1978. (c) Horspool, W. M.; Armesto, D. Organic Photochemistry; Ellis Horwood and PTR Prentice Hall: Chichester, England, 1992. (d) CRC Handbook of Organic Photochemistry and Photobiology; Horspool, W. M., Song, P., Ed.; CRC Press: Boca Raton, FL, 1995.
    • (1995) CRC Handbook of Organic Photochemistry and Photobiology
    • Horspool, W.M.1    Song, P.2
  • 7
    • 85052773289 scopus 로고
    • Padwa, A., Ed.; Marcel Dekker: New York
    • (c) Demuth, M. In Organic Photochemistry; Padwa, A., Ed.; Marcel Dekker: New York, 1991; Vol. 11, pp 37-109.
    • (1991) Organic Photochemistry , vol.11 , pp. 37-109
    • Demuth, M.1
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    • 0003533887 scopus 로고
    • Padwa, A., Ed.; Marcel Dekker: New York
    • Kropp, P. J. In Organic Photochemistry; Padwa, A., Ed.; Marcel Dekker: New York, 1979; VoL 4, p 1.
    • (1979) Organic Photochemistry , vol.4 , pp. 1
    • Kropp, P.J.1
  • 33
    • 85033849857 scopus 로고    scopus 로고
    • note
    • It is difficult at this point to explain why aldehyde 6 undergoes the ODPM rearrangement while the analogous methyl ketone 22 does not. It will be necessary to carry out additional studies in order to establish the possible analogies and differences between the reactivity of β,γ-unsaturated aldehydes and ketones before giving a reasonable explanation for this observation.
  • 43
    • 85033863019 scopus 로고    scopus 로고
    • note
    • 19,22,23 Apparently, the same factors that control the stereochemistry of these compounds in the triplet excited state also operate for β,γ-unsaturated aldehydes.


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