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

Michal Shmulinson, Astrid Pilz, Moris S. Eisen*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

10 Scopus citations

Abstract

The reaction of C6F5CN with the dimeric lithium salt [Li(NSiMe3)·Et2O]2 yielded a 11:9 mixture of (Me3Si)2NC6F4CN-41 and LiN(C6F4CN-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 SiMe3F, 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.

Original languageEnglish
Pages (from-to)2483-2486
Number of pages4
JournalJournal of the Chemical Society. Dalton Transactions
Issue number14
DOIs
StatePublished - 21 Jul 1997
Externally publishedYes

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