| Abstract
| - The reaction of 2-picoline at the methyl group with NDA and KDA followed by dimethyldisulfide trappingfurnished, respectively, dithioacetals and trithioortho esters with high selectivity. The method wassuccessfully applied to other methyl-substituted pyridines, quinolines, and pyrazines. Dithioketals wereprepared by a one-pot procedure involving the reaction of metalated 2-picoline with 2 equiv ofdimethyldisulfide followed by in situ trapping with a second electrophile. All of the generated thio-substituted compounds were efficiently transformed in presence of mercury salts or under oxidizingconditions to other functional groups comprising aldehydes, ketones, ketals, thiol esters, orthoesters, andesters.
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