Synthesis, characterization and crystal structures of boron-containing intermediates in the reductive amination of ferrocenecarboxaldehyde to a bis(ferrocenylmethyl) amine |
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Authors: | Nathan C Tice |
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Institution: | Department of Chemistry, University of Kentucky, 125 Chemistry-Physics Building, Lexington, KY 40506-0055, United States |
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Abstract: | Reaction of ferrocenecarboxaldehyde with aqueous methylamine leads to (methylimino)methyl]ferrocene, which is reduced to N-(ferrocenylmethyl)-N-methylamine by NaBH4. This amine reacts with ferrocenecarboxaldehyde and NaCNBH3 to give the tertiary ammonium salt, di(N-(ferrocenylmethyl))-N-methylammonium cyanoborohydride. Hydrolysis of the NaCNBH3 reaction mixture produces the free amine, di(N-(ferrocenylmethyl))-N-methylamine. Thermolysis of di(N-(ferrocenylmethyl))-N-methylammonium cyanoborohydride in refluxing tetrahydrofuran converts it to the cyanoborane adduct, di(N-ferrocenylmethyl)-N-methylamine-cyanoborane, with elimination of H2. The new compounds are fully characterized by using spectroscopic and physical methods, including X-ray crystal structure determinations of di(N-(ferrocenylmethyl))-N-methylammonium cyanoborohydride, di(N-(ferrocenylmethyl))-N-methylamine, and di(N-(ferrocenylmethyl))-N-methylamine-cyanoborane. |
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Keywords: | Ferrocene Reductive amination Ammonium cyanoborohydride Amine-cyanoborane adduct X-ray crystal structure NMR spectroscopy |
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