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CC-BY - Uznanie autorstwaResearch into the oxidation of abietic acid–derived enone with atmospheric oxygen
| dc.abstract.en | This work presents results of methyl 7-oxoabiet-13(14)-en-18-oate (3) selfoxidation 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 indepth 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. |
| dc.affiliation | Uniwersytet Warszawski |
| dc.contributor.author | Trzybiński, Damian |
| dc.contributor.author | Kuśmirek, Damian |
| dc.contributor.author | MASNYK, Marek |
| dc.contributor.author | FRELEK, Jadwiga |
| dc.date.accessioned | 2024-01-25T19:13:14Z |
| dc.date.available | 2024-01-25T19:13:14Z |
| dc.date.copyright | 2020-01-08 |
| dc.date.issued | 2020 |
| dc.description.accesstime | AT_PUBLICATION |
| dc.description.finance | Publikacja bezkosztowa |
| dc.description.number | 4 |
| dc.description.version | FINAL_PUBLISHED |
| dc.description.volume | 32 |
| dc.identifier.doi | 10.1002/CHIR.23176 |
| dc.identifier.issn | 0899-0042 |
| dc.identifier.uri | https://repozytorium.uw.edu.pl//handle/item/118452 |
| dc.identifier.weblink | https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fchir.23176 |
| dc.language | eng |
| dc.pbn.affiliation | chemical sciences |
| dc.relation.ispartof | Chirality |
| dc.relation.pages | 437-445 |
| dc.rights | CC-BY |
| dc.sciencecloud | nosend |
| dc.subject.en | abietic acid |
| dc.subject.en | aerobic oxidation |
| dc.subject.en | autooxidation |
| dc.subject.en | enones |
| dc.subject.en | hydroperoxides |
| dc.title | Research into the oxidation of abietic acid–derived enone with atmospheric oxygen |
| dc.type | JournalArticle |
| dspace.entity.type | Publication |