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Research into the oxidation of abietic acid–derived enone with atmospheric oxygen
Author(s) -
Masnyk Marek,
Kuśmirek Damian,
Trzybiński Damian,
Frelek Jadwiga
Publication year - 2020
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.23176
Subject(s) - chemistry , abietane , triethylamine , enone , abietic acid , cyclohexenone , base (topology) , oxygen , photochemistry , organic chemistry , resin acid , rosin , diterpene , mathematical analysis , mathematics
This work presents results of methyl 7‐oxoabiet‐13(14)‐en‐18‐oate ( 3 ) self‐oxidation with air‐oxygen in the presence of various bases such as triethylamine or sodium t ‐butoxide. While under aerobic conditions, the use of sodium t ‐butoxide as a base results in the formation of four isomeric alcohols, an addition of triethylamine into reaction medium directs the enone 3 oxidation to hydroperoxides. To clarify this base dependence and to obtain more in‐depth information about this reaction additional studies with cyclohexenone as a reference enone have been undertaken. Their results demonstrated the predisposition of abietane hydroperoxides to oxidize α,β‐unsaturated ketones to epoxides in the presence of t ‐butoxide while reducing the hydroperoxide group to hydroxyl. This ability of hydroperoxides to epoxidize conjugated double bonds and confirmed by the present study intermolecular course allowed proposing a plausible mechanism for this reaction.