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A Fischer-Type Ruthenium Carbene Complex as a Metathesis Catalyst for the Synthesis of Enol Ethers

作   者:
Wang, Xia-LinChiang, Nicholas YichingPeng, Jian-JhihYu, LeiXu, Li-JunYang, Hau-RenJin, Bih-YawZhang, PingluLai, Yu-YingLi, ZeLai, Guo-QiaoLuh, Tien-Yau
作者机构:
Hangzhou Normal UnivNatl Taiwan Univ
关键词:
CROSS-METATHESISINTERMEDIATES RELEVANTPOLYNORBORNENESRING-OPENING/CROSS-METATHESISOLEFIN-METATHESISCLOSING METATHESISNORBORNENE DERIVATIVESPOLYMERIZATION ROMPRUTHENACYCLOBUTANEINSIGHTS
期刊名称:
The Journal of Organic Chemistry
i s s n:
0022-3263
年卷期:
2021 年 86 卷 24 期
页   码:
17629-17639
页   码:
摘   要:
The Grubbs G-I or G-II catalyst gives the ruthenium ethoxy carbene complex, which catalyzes ring-opening cross metathesis (ROCM) of a strained cyclic alkene to give a diene where one of the two alkene moieties in the product contains an ethoxy substituent. No polymeric products are detected. Hydrocarbons such as parent norbornene or substituted cyclo- propenes can proceed with the reaction smoothly. Tertiary amines, N-alkylimides, esters, and aryl or alkyl bromides remain intact under the reaction conditions. In addition to vinyl ethers, vinylic esters can also be used. The time required to reach a 50% yield of the ROCM product t(50) varies from 0.01 to 140 h depending on the strain and nucleophilicity of the double bond. Anchimeric participation of an electron-rich group would result in significant enhancement of the reactivity, and the t(50) could be as short as several minutes. A similar substrate without such a neighboring group shows a much slower rate. An exo-norborne derivative reacts much faster than the corresponding endo-isomer. Alkenes with poor nucleophilicity are less favored for the ROCM process, so is less strained cyclooctene.
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