On the formation of a side product with hexahydroaporphine-like structure in the Grewe cyclization of dextromethorphan
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- 作者：Qiao Zhao ; Kai Zhao ; Sheng-ying Wu ; Bo-xue Tian…
- 关键词：Grewe cyclization ; Dextromethorphan ; Hexahydroaporphine ; like side product ; DFT calculation
- 刊名：Research on Chemical Intermediates
- 出版年：2017
- 出版时间：March 2017
- 年：2017
- 卷：43
- 期：3
- 页码：1689-1708
- 全文大小：
- 刊物类别：Chemistry and Materials Science
- 刊物主题：Catalysis; Physical Chemistry; Inorganic Chemistry;
- 出版者：Springer Netherlands
- ISSN：1568-5675
- 卷排序：43
文摘
Factors leading to the formation of a hexahydroaporphine-like cyclizing side product were studied systematically for the first time and the ratio of this side product was controlled effectively. To understand better the electronic effect of substrates on the formation of side products, different 1-benzyloctahydroisoquinolines with substituted groups on nitrogen or benzene ring were compared. A plausible mechanism of cyclizing reaction was proposed, and key intermediates as well as transition states were analyzed using DFT calculations.