Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Regioselective 1,3-Dipolar Cycloaddition and 1,2-Addition between Benzaldoxime NH-nitrone and Perfluoro-2-methyl-2-pentene

  • Received : 2009.04.23
  • Accepted : 2010.02.24
  • Published : 2010.05.20
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Abstract

Regioselective perfluorinated [3+2] cycloadducts and 1,2-adducts have been prepared by 1,3-dipolar cycloaddition between benzaldoxime NH-nitrone and perfluorinated alkene, perfluoro-2-methyl-2-pentene. Although the cycloaddition reaction is carried out at room temperature, the corresponding perfluorinated compounds are effectively produced in a high yield. In particular, the methoxy-substituted adducts (4 and 7a) show the self-assembled structure by intermolecular interactions. These derivatives were characterized by IR, $^1H$ and $^{19}F$ NMR, and the absolute structure of perfluorinated adducts was confirmed by X-ray crystallography.

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References

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Cited by

  1. ChemInform Abstract: Regioselective 1,3‐Dipolar Cycloaddition and 1,2‐Addition Between Benzaldoxime NH‐Nitrone and Perfluoro‐2‐methyl‐2‐pentene. vol.41, pp.40, 2010, https://doi.org/10.1002/chin.201040126
  2. On the Question of Zwitterionic Intermediates in the [3 + 2] Cycloaddition Reactions between C-arylnitrones and Perfluoro 2-Methylpent-2-ene vol.26, pp.23, 2010, https://doi.org/10.3390/molecules26237147