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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 31, Number 5
BKCSDE 31(5)
May 20, 2010

Title	Synthesis of Perfluorinated Heterocyclic Compounds Having a Long Alkyl Chain Functionality by 1,3-Dipolar Cycloaddition
Author	Chan Woo Lee, Ho Yun Hwang, Joo Yuen Park, Ki Whan Chi
Keywords	Perfluorinated long alkyl, Isoxazoline, Isoxazolidine, Cycloaddition
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 ¹⁹F NMR, and MASS analysis.
Page	1305 - 1308
Full Text	PDF

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