Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Synthesis of Perfluorinated Heterocyclic Compounds Having a Long Alkyl Chain Functionality by 1,3-Dipolar Cycloaddition

  • Received : 2009.04.29
  • Accepted : 2010.02.24
  • Published : 2010.05.20
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Abstract

Regioselective perfluorinated isoxazolidine (5 and 7), isoxazoline (9) and 1,2-addition products (6 and 8) having a long alkyl chain functionality have been prepared by 1,3-dipolar cycloaddition between a 1,3-dipole (NH-nitrone or nitrile oxide) and dipolarophile (perfluoro-2-methyl-2-pentene or styrene), respectively. Interestingly, unusual extended conjugated form of isoxazoline adduct (10) was obtained by dehydrofluorinated reaction from the corresponding perfluorinated isoxazoline adduct (9) which was derived from cycloadition between the perfluorinated long alkyl nitrile oxide 1,3-diplole and styrene olefin. This synthetic methodology of heterocyclic compound having a long alkyl chain functionality is useful for the designing of synthetic strategy and potential self-assembled monolayers (SAM) application. These derivatives were characterized by IR, $^1H$ and $^{19}F$ NMR, and MASS analysis.

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References

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Cited by

  1. ChemInform Abstract: Synthesis of Perfluorinated Heterocyclic Compounds Having a Long Alkyl Chain Functionality by 1,3‐Dipolar Cycloaddition. vol.41, pp.40, 2010, https://doi.org/10.1002/chin.201040127