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Preference for Syn Ene Additions of 1 O 2 to Trisubstituted, Acyclic Olefins
Author(s) -
SchulteElte Karl H.,
Muller Bernard L.,
Rautenstrauch Valentin
Publication year - 1978
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19780610805
Subject(s) - chemistry , ene reaction , olefin fiber , medicinal chemistry , stereochemistry , organic chemistry , catalysis
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.