Research into the oxidation of abietic acid-derived enone with atmospheric oxygen

编号 020028004

推送时间 20210301

研究领域 林产化工 

年份 2021 

类型 期刊 

语种 英语

标题 Research into the oxidation of abietic acid-derived enone with atmospheric oxygen

来源期刊 Chirality

期 第280期

发表时间 20200203

关键词 abietic acid;  aerobic oxidation;  autooxidation;  enones;  hydroperoxides; 

摘要 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.

服务人员 尚玮姣

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