Haloacyl Complexes of Boron, [(CF3)3BC(O)Hal]− (Hal=F, Cl, Br, I)

Finze, Maik; Bernhardt, Eduard; Willner, Helge; Lehmann, Christian W.

doi:10.1002/chem.200500038

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Haloacyl Complexes of Boron, [(CF₃)₃BC(O)Hal]⁻ (Hal=F, Cl, Br, I)

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Lehmann, Christian W.
Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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引用

Finze, M., Bernhardt, E., Willner, H., & Lehmann, C. W. (2005). Haloacyl Complexes of Boron, [(CF₃)₃BC(O)Hal]⁻ (Hal=F, Cl, Br, I). Chemistry – A European Journal, 11(22), 6653-6665. doi:10.1002/chem.200500038.

引用: https://hdl.handle.net/11858/00-001M-0000-000F-952D-8

要旨

The haloacyltris(trifluoromethyl)borate anions [(CF₃)₃BC(O)Hal]⁻ (Hal=F, Cl, Br, I) have been synthesized by reacting (CF₃)₃BCO with either MHal (M=K, Cs; Hal=F) in SO₂ or MHal (M=[nBu₄N]⁺, [Et₄N]⁺, [Ph₄P]⁺; Hal=Cl, Br, I) in dichloromethane. Metathesis reactions of the fluoroacyl complex with Me₃SiHal (Hal=Cl, Br, I) led to the formation of its higher homologues. The thermal stabilities of the haloacyltris(trifluoromethyl)borates decrease from the fluorine to the iodine derivative. The chemical reactivities decrease in the same order as demonstrated by a series of selected reactions. The new [(CF₃)₃BC(O)Hal]⁻ (Hal=F, Cl, Br) salts are used as starting materials in the syntheses of novel compounds that contain the (CF₃)₃B-C fragment. All borate anions [(CF₃)₃BC(O)Hal]⁻ (Hal=F, Cl, Br, I) have been characterized by multinuclear NMR spectroscopy (¹¹B, ¹³C, ¹⁷O, ¹⁹F) and vibrational spectroscopy. [PPh₄][(CF₃)₃BC(O)Br] crystallizes in the monoclinic space group P2/c (no. 13) and the bond parameters are compared with those of (CF₃)₃BCO and K[(CF₃)₃BC(O)F]. The interpretation of the spectroscopic and structural data are supported by DFT calculations [B3LYP/6‐311+G(d)].