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Preference for Syn Ene Additions of 1O2 to Trisubstituted, Acyclic Olefins

✍ Scribed by Karl H. Schulte-Elte; Bernard L. Muller; Valentin Rautenstrauch

Publisher
John Wiley and Sons
Year
1978
Tongue
German
Weight
433 KB
Volume
61
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Dye‐sensitized photooxygenations of 3 pairs of (E)/(Z) trisubstituted olefins were studied in order to establish the partitioning between the 3 possible ene additions. The (E)‐isomers underwent only the 2 ene additions (>95%) involving H‐atom abstractions at the same, disubstituted side of the olefins, termed syn ene additions, with almost equal ease. The (Z)‐isomers underwent mainly (85‐90%) the syn ene additions, with the ones leading to the tertiary hydroperoxides distinctly favoured, and some (10‐15%)ene additions at the monosubstituted side of the olefin, termed anti ene addition.

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