α-Methyl Functionalization of Electron-Poor Heterocycles: Chloromethyl Derivatives of 2,2'-Bipyridines

Article abstract of DOI:10.1021/jo00142a022

The syntheses of 6-(chloromethyl)- (3), 6-(chloromethyl)-6'-methyl- (2), and 6,6'-bis(chloromethyl)-2,2'-bipyridine (1) are reported.Complete spectral analyses including ¹H and ¹³C NMR data are given for each compound.Experimental results and appropriate comparisons justify the reassignment of the ¹³C NMR spectral data for the bipyridine derivatives.Description of the synthetic techniques with the new, critical modifications utilized to prepare these key starting materials are presented.Bipyridine N-oxides have been shown to undergo intra-ring rearrangements; no N-oxide migration occurs under thermolysis at 200 deg C.