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gamma-Ray irradiation of a binary solution consisting of pyridine and methanol caused almost no reaction of pyridine.However, the addition of a catalytic amount of nickel nitrate to this binary solution induced the alpha-methylation of pyridine in good yield upon gamma-ray irradiation at room temperature either in air or in vacuo.This alpha-methylation gave alpha-picoline as a major product.The yield of alpha-picoline increased with increase in the irradiation time at the initial stage of the reaction, reached a maximum (27.8percent) at an irradiation duration of between 8 and 10h, and then decreased progressively at greater irradiation times.In addition, the yield of alpha-picoline at a given irradiation time showed a tendency to increase with increasing amount of the nickel nitrate catalyst or with increasing fraction of methanol in the starting solution. gamma-Ray irradiation in the presence of nickel nitrate was also found to induce the catalytic alpha-methylation of gamma-picoline with methanol at room temperature either in air or in vacuo, giving 2,4-lutidine as a major product in a maximum yield of 8.3percent.Further, the demethylation reaction of alpha-picoline to pyridine and that of 2,4-lutidine to gamma-picoline were also promoted greatly upon gamma-ray irradiation at room temperature in air in the presence of both methanol and nickel nitrate.

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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis