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
A. Nickon and W. L. Mendelson: J. Amer. chem. Soc. 87, 3921 (1965).
H. H. Wasserman and A. Liberles: J. Amer. chem. Soc. 82, 2086 (1960).
R. E. Lutz, W. J. Welstead, jr., R. G. Bass and J. I. Dale: J. Org. Chem. 27, 1111 (1962).
D. M. Frankel, C. E. Johnson and H. M. Pitt: J. Org. Chem. 22, 1119 (1957).
C. Dufraisse, A. Étienne and J.-J. Basselier: Comptes rendus 244, 2209 (1957).
J.-J. Basselier: Comptes rendus 258, 2851 (1964).
S. Bodforss: Ber. dtsch. chem. Ges. 51, 214 (1918).
O. Jeger, K. Schaffner and H. Wehrli: Pure Appl. Chem. 9, 555 (1964).
H. Wehrli, C. Lehmann, K. Schaffner and O. Jeger: Helv. Chim. Acta 47, 1336 (1964).
H. E. Zimmerman, B. R. Cowley, C.-Y. Tseng and J. W. Wilson: J. Amer. chem. Soc. 86, 947 (1964).
C. K. Johnson, B. Dominy and W. Reusch: J. Amer. chem. Soc. 85, 3894 (1963).
C. Djerassi, W. Klyne, T. Norin, G. Ohloff and E. Klein: Tetrahedron 21, 163 (1965).
A. Padwa: J. Amer. chem. Soc. 87, 4205 (1965).
A. Padwa: Tetrahedron Letters 1964, 813.
A. Padwa and R. Hartman: J. Amer. chem. Soc. 86, 4212 (1964).
J. M. Dunston and P. Yates: Tetrahedron Letters 1964, 505.
R. Pütter and W. Dilthey: J. prakt. Chem. [2] 149, 183 (1937).
E. F. Ullman: J. Amer. chem. Soc. 85, 3529 (1963).
E. F. Ullman and J. E. Milks: J. Amer. chem. Soc. 84, 1315 (1962).
E. F. Ullman and J. E. Milks: J. Amer. chem. Soc. 86, 3814 (1964).
H. E. Zimmerman and R. D. Simkin: Tetrahedron Letters 1964, 1847.
E. Weitz and A. Scheffer: Ber. dtsch. chem. Ges. 54, 2327 (1921).
R. Pütter and W. Dilthey: J. prakt. Chem. [2] 150, 40 (1937).
C. Lehmann, K. Schaffner and O. Jeger: Helv. Chim. Acta 45, 1031 (1962).
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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
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