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Photochemical formation and transformations of epoxides

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Preparative Organic Photochemistry
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Abstract

Epoxides appearing among the photooxidation products of olefins are usually resulting from secondary reactions of the intermediate hydroperoxides or epidioxides. Epoxides may form from these intermediates either by rearrangement or via a Prileshajew type reaction with unconsumed olefin. The formation of steroid epoxyketones [1] and of epoxides in the pyrrole [2] and furan [2, 3] series has been mentioned in the pertinent chapters (39 and 42). Hence, only a few further examples of photochemical epoxide formation will be discussed in the following text.

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References

  1. A. Nickon and W. L. Mendelson: J. Amer. chem. Soc. 87, 3921 (1965).

    Article  CAS  Google Scholar 

  2. H. H. Wasserman and A. Liberles: J. Amer. chem. Soc. 82, 2086 (1960).

    Article  CAS  Google Scholar 

  3. R. E. Lutz, W. J. Welstead, jr., R. G. Bass and J. I. Dale: J. Org. Chem. 27, 1111 (1962).

    CAS  Google Scholar 

  4. D. M. Frankel, C. E. Johnson and H. M. Pitt: J. Org. Chem. 22, 1119 (1957).

    Article  CAS  Google Scholar 

  5. C. Dufraisse, A. Étienne and J.-J. Basselier: Comptes rendus 244, 2209 (1957).

    CAS  Google Scholar 

  6. J.-J. Basselier: Comptes rendus 258, 2851 (1964).

    CAS  Google Scholar 

  7. S. Bodforss: Ber. dtsch. chem. Ges. 51, 214 (1918).

    Article  CAS  Google Scholar 

  8. O. Jeger, K. Schaffner and H. Wehrli: Pure Appl. Chem. 9, 555 (1964).

    Article  CAS  Google Scholar 

  9. H. Wehrli, C. Lehmann, K. Schaffner and O. Jeger: Helv. Chim. Acta 47, 1336 (1964).

    Article  Google Scholar 

  10. H. E. Zimmerman, B. R. Cowley, C.-Y. Tseng and J. W. Wilson: J. Amer. chem. Soc. 86, 947 (1964).

    Article  CAS  Google Scholar 

  11. C. K. Johnson, B. Dominy and W. Reusch: J. Amer. chem. Soc. 85, 3894 (1963).

    Article  CAS  Google Scholar 

  12. C. Djerassi, W. Klyne, T. Norin, G. Ohloff and E. Klein: Tetrahedron 21, 163 (1965).

    Article  CAS  Google Scholar 

  13. A. Padwa: J. Amer. chem. Soc. 87, 4205 (1965).

    Article  CAS  Google Scholar 

  14. A. Padwa: Tetrahedron Letters 1964, 813.

    Google Scholar 

  15. A. Padwa and R. Hartman: J. Amer. chem. Soc. 86, 4212 (1964).

    Article  CAS  Google Scholar 

  16. J. M. Dunston and P. Yates: Tetrahedron Letters 1964, 505.

    Google Scholar 

  17. R. Pütter and W. Dilthey: J. prakt. Chem. [2] 149, 183 (1937).

    Article  Google Scholar 

  18. E. F. Ullman: J. Amer. chem. Soc. 85, 3529 (1963).

    Article  CAS  Google Scholar 

  19. E. F. Ullman and J. E. Milks: J. Amer. chem. Soc. 84, 1315 (1962).

    Article  CAS  Google Scholar 

  20. E. F. Ullman and J. E. Milks: J. Amer. chem. Soc. 86, 3814 (1964).

    Article  CAS  Google Scholar 

  21. H. E. Zimmerman and R. D. Simkin: Tetrahedron Letters 1964, 1847.

    Google Scholar 

  22. E. Weitz and A. Scheffer: Ber. dtsch. chem. Ges. 54, 2327 (1921).

    Article  Google Scholar 

  23. R. Pütter and W. Dilthey: J. prakt. Chem. [2] 150, 40 (1937).

    Article  Google Scholar 

  24. C. Lehmann, K. Schaffner and O. Jeger: Helv. Chim. Acta 45, 1031 (1962).

    Article  CAS  Google Scholar 

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Schönberg, A. (1968). Photochemical formation and transformations of epoxides. In: Preparative Organic Photochemistry. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-87918-0_40

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  • DOI: https://doi.org/10.1007/978-3-642-87918-0_40

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-642-87920-3

  • Online ISBN: 978-3-642-87918-0

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