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Issue 14, 1997
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Carbon–fluorine bond activation in perfluorobenzonitrile byLiN(SiMe3)2. Synthesis of(Me3Si)2NC6F4CN-4 andcrystal structure ofLiN(C6F4CN-4)2·2C4H8O

Abstract

The reaction of C 6 F 5 CN with the dimeric lithium salt [Li(NSiMe 3 )·Et 2 O] 2 yielded a 11∶9 mixture of (Me 3 Si) 2 NC 6 F 4 CN-4 1 and LiN(C 6 F 4 CN-4) 2 ·2thf, respectively (thf = tetrahydrofuran). The compounds were characterized spectroscopically and complex 2 by crystal structure determination. The central lithium forms a distorted trigonal bipyramid the apical position of which is filled by a nitrile nitrogen of an adjacent molecule, inducing chains running parallel to the b-direction of the crystal. The driving force for the production of 1 and 2 is the elimination of LiF and SiMe 3 F, respectively. The calculated enthalpy for formation of 2 is more favourable compared to that for formation of 1, although the similar yields indicate that similar enthalpies of activation apply to both systems.

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Article type: Paper
DOI: 10.1039/A700682I
J. Chem. Soc., Dalton Trans., 1997, 2483-2486

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    Carbon–fluorine bond activation in perfluorobenzonitrile by LiN(SiMe3)2. Synthesis of (Me3Si)2NC6F4CN-4 and crystal structure of LiN(C6F4CN-4)2·2C4H 8O

    M. Shmulinson, A. Pilz and M. S. Eisen, J. Chem. Soc., Dalton Trans., 1997, 2483
    DOI: 10.1039/A700682I

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