Ag(I)-Catalyzed Regioselective Ring-Opening of N-Tosylaziridine and N-Tosylazetidine with S-, O-, and N-Nucleophiles and Tethered Dinucleophiles
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- 作者：Milan Bera ; Sanjay Pratihar ; Sujit Roy
- 刊名：Journal of Organic Chemistry
- 出版年：2011
- 出版时间：March 4, 2011
- 年：2011
- 卷：76
- 期：5
- 页码：1475-1478
- 全文大小：854K
- 年卷期：v.76,no.5(March 4, 2011)
- ISSN：1520-6904
文摘
[Ag(COD)2]PF6 catalyzes the ring-opening of N-tosylaziridines and -azetidines with alcohols, amines, thiols, and related tethered 1,2-ethane dinucleophiles. Initial rate studies and DFT-based evaluation of stepwise energetics suggest an inverse relationship between the nucleophilic reactivity of a heteroatom donor and its binding affinity to cationic Ag(I).