Mechanisms of the InCl3-Catalyzed Type-I, II, and III Cycloisomerizations of 1,6-Enynes | |
Zhuo, Lian-Gang; Zhang, Ji-Ji; Yu, Zhi-Xiang | |
刊名 | JOURNAL OF ORGANIC CHEMISTRY
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2014-05-02 | |
卷号 | 79期号:9页码:3809-3820 |
ISSN号 | 0022-3263 |
DOI | 10.1021/jo500059j |
英文摘要 | InCl3-catalyzed cycloisomerizations of 1,6-enynes can give either type-I dienes and cyclohexenes (type-III dienes), or type-II dienes, depending on the substitutions in the substrates. Previously, we studied how the type-II diene products were generated and found that the real catalytic species for the cycloisomerizations is InCl2+ (J. Org. Chem. 2012, 77, 8527-8540). In the present paper, we used density functional theory (DFT) calculations to reveal how the type-I and type-III dienes were generated. A unified model to explain how substituents affect the regiochemistry of type-I, II, and III cycloisomerizations has been provided. Experimental and computational investigation of the InCl3-catalyzed cycloisomerization of 1,6-enynes with both substituents at the alkyne and alkene parts has also been reported in the present study. |
语种 | 英语 |
出版者 | AMER CHEMICAL SOC |
WOS记录号 | WOS:000335490700009 |
内容类型 | 期刊论文 |
源URL | [http://ir.iccas.ac.cn/handle/121111/50529] ![]() |
专题 | 中国科学院化学研究所 |
通讯作者 | Yu, Zhi-Xiang |
作者单位 | Peking Univ, BNLMS, Key Lab Bioorgan Chem & Mol Engn, Minist Educ,Coll Chem, Beijing 100871, Peoples R China |
推荐引用方式 GB/T 7714 | Zhuo, Lian-Gang,Zhang, Ji-Ji,Yu, Zhi-Xiang. Mechanisms of the InCl3-Catalyzed Type-I, II, and III Cycloisomerizations of 1,6-Enynes[J]. JOURNAL OF ORGANIC CHEMISTRY,2014,79(9):3809-3820. |
APA | Zhuo, Lian-Gang,Zhang, Ji-Ji,&Yu, Zhi-Xiang.(2014).Mechanisms of the InCl3-Catalyzed Type-I, II, and III Cycloisomerizations of 1,6-Enynes.JOURNAL OF ORGANIC CHEMISTRY,79(9),3809-3820. |
MLA | Zhuo, Lian-Gang,et al."Mechanisms of the InCl3-Catalyzed Type-I, II, and III Cycloisomerizations of 1,6-Enynes".JOURNAL OF ORGANIC CHEMISTRY 79.9(2014):3809-3820. |
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