AN UNUSUAL OXIDATION OF AN N-CH3 GROUP TO AN N-CHO GROUP BY OSMIUM TETROXIDE

Article abstract of DOI:10.1016/S0040-4039(00)88711-0

Treatment of pyrodelphinine (1) with osmium tetroxide afforded a mixture of the cis-hydroxylation product 2 and an unexpected product 3 in the ratio of 4:1, respectively.Similarly, oxidation of delphinine (5) afforded α-oxodelphinine (6; 75percent) and oxidation of mesaconitine (8) furnished oxonitine (9; 92percent).Thus a very selective oxidation of the N-methyl group of delphinine and mesaconitine is effected by osmium tetroxide.