Mamane, Victor Aubert, Emmanuel Fort, Yves The Methyl Group as a Source of Structural Diversity in Heterocyclic Chemistry:  Side Chain Functionalization of Picolines and Related Heterocycles The reaction of 2-picoline at the methyl group with NDA and KDA followed by dimethyldisulfide trapping furnished, respectively, dithioacetals and trithioortho esters with high selectivity. The method was successfully applied to other methyl-substituted pyridines, quinolines, and pyrazines. Dithioketals were prepared by a one-pot procedure involving the reaction of metalated 2-picoline with 2 equiv of dimethyldisulfide 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 oxidizing conditions to other functional groups comprising aldehydes, ketones, ketals, thiol esters, orthoesters, and esters. Methyl Group;methyl group;2 equiv;thiol esters;dimethyldisulfide;Structural Diversity;KDA;Related Heterocycles;trithioortho esters;picoline;NDA;mercury salts;oxidizing conditions 2007-09-14
    https://acs.figshare.com/articles/dataset/The_Methyl_Group_as_a_Source_of_Structural_Diversity_in_Heterocyclic_Chemistry_Side_Chain_Functionalization_of_Picolines_and_Related_Heterocycles/2985883
10.1021/jo071209z.s007