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  • Title: Enantioselective synthesis of an all-syn four vicinal fluorine motif.
    Author: Hunter L, O'Hagan D, Slawin AM.
    Journal: J Am Chem Soc; 2006 Dec 27; 128(51):16422-3. PubMed ID: 17177350.
    Abstract:
    Alkanes bearing multiple vicinal fluorine atoms at adjacent stereocenters may be considered intermediate between alkanes and perfluoroalkanes, and as a class, their chemistry and behavior remain to be explored. We report here a stereoselective synthesis of an all-syn four vicinal fluorine motif as a single enantiomer. The four vicinal fluorine compound was amenable to single-crystal X-ray analysis, and the resulting structure displays gauche relationships between all four fluorines, consistent with the fluorine gauche effect, and CF...HC hydrogen bonding between adjacent fluoroalkyl chains.
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