Bulletin of the Korean Chemical Society

  • 제31권5호
  • /
  • Pages.1305-1308
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  • 2010
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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Synthesis of Perfluorinated Heterocyclic Compounds Having a Long Alkyl Chain Functionality by 1,3-Dipolar Cycloaddition

  • 투고 : 2009.04.29
  • 심사 : 2010.02.24
  • 발행 : 2010.05.20
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초록

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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참고문헌

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피인용 문헌

  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