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In the presence of water lithium tetrahydroborate is capable of reducing pyridine to 1,4- dihydropyridine. The product, lithiumtetrakis(pyridine) tetrakis(1,4-hydropyridyl)borate, was isolated and characterized by NMR and IR spectroscopy and single crystal X-ray diffraction. [Li(py) 4 ][B(pyH) 4 ].2(1,4-dioxane) crystallized in space group P4 2 /n, Z = 2. Similarly, NaBH4 can also reduce pyridine in the presence of water and equivalent amounts of LiCl or ZnCl 2 .

The Reduction of Pyridine to 1,4-Dihydropyridine by Lithiumtetrahydroborate in the Presence of Water