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• W2023338323 abstract "The reaction of [B12H11NH3]-, the amino derivative of the closo-dodecaborate anion, with aldehydes in methanol in the presence of catalytic amounts of alkali gives N-protonated Schiff bases [B12H11NHCHR]- (R = C6H5, 2-C6H4OMe, 4-C6H4OMe, 4-C6H4SMe, 4-C6H4NMe2, 4-C6H4NHCOMe, 4-C6H4CN, 4-C6H4Br, 4-C6H4Cl, 3,4-C6H3O2CH2, 1-C10H7, 2-C10H7, CHCHMe, CHCHPh). Reduction of the Schiff bases with NaBH4 in aqueous 2-propanol gives quantitatively the corresponding monoalkylamino derivatives [B12H11NH2CH2R]- (R = 2-C6H4OMe, 3,4-C6H3O2CH2, 4-C6H4NHCOMe, 4-C6H4CN). closo-Dodecaborate derivatives containing amino, carboxy, and isothiocyanate functions on aromatic rings, [B12H11NH2CH2C6H4-4-NH2]-, [B12H11NH2CH2C6H4-4-COOH]-, and [B12H11NH2CH2C6H4-4-NCS]-, were prepared. Functionalized derivatives of the [B12H12]2- anion can be used in BNCT and as a linker for iodination and astatination of biomolecules for radioimmunodetection and for radioimmunotherapy. The structures of Schiff bases (Bu4N)[B12H11NHCHC6H4-4-NMe2]*CHCl3 (I) and (Bu4N)[B12H11NHCHC6H4-2-OMe] (II) were determined by single-crystal X-ray diffraction. I crystallizes in the monoclinic space group P21/c with Z = 4 and unit cell dimensions a = 11.465(6) Å, b = 21.314(7) Å, c = 16.625(6) Å, β = 101.38(3)°. Crystals II belong to the monoclinic space group P21/c system, a = 10.282(2) Å, b = 20.272(5) Å, c = 17.052(3) Å, β = 105.31(2)°, Z = 4. The trans configuration of the protonated imino group was established (B−N = 1.517(7) and 1.525(4) Å, N−Cim = 1.274(6) and 1.274(3) Å, Cim−Car = 1.421(7) and 1.437(4) Å, for I and II, respectively). A strong intramolecular hydrogen bond between the imine hydrogen and the methoxy oxygen in the ortho position of the benzene ring (N···O = 2.714(4) Å, N−H = 0.93(2) Å, HN···O = 1.98(2) Å, N−H···O = 135(2)°) was found in II." @default.
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• W2023338323 date "1999-11-23" @default.
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• W2023338323 title "Synthesis of Schiff Bases Derived from the Ammoniaundecahydro-<i>closo</i>-dodecaborate(1−) Anion, [B₁₂H₁₁NHCHR]^-, and Their Reduction into Monosubstituted Amines [B₁₂H₁₁NH₂CH₂R]^-: A New Route to Water Soluble Agents for BNCT" @default.
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• W2023338323 doi "https://doi.org/10.1021/ic990013h" @default.
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