Alkylation and Sulfenylation of Amino Thioethers. Tetrahydro-1,3-thiazine and Related Compounds

Article abstract of DOI:10.1021/jo00268a039

Reactions of electrophiles with several amino thioethers of varying chain length and ring structure are described.The reactants include N,N-dimethylmethanesulfenamide, <<(N,N-dimethylamino)methyl>thio>methane, 1-(N,N-dimethylamino)-2-(methylthio)ethane, tetrahydro-1,3-thiazine, tetrahydro-2-methyl-1,3-thiazine, and the corresponding N-methyl and N-acetyl derivatives.Electrophiles include methyl iodide, ethyl iodide, 3-chloro- and 3-bromopropene, trimethyloxonium fluoroborate, methanesulfenyl chloride, and dimethyl(methylthio)sulfonium fluoroborate.The objective was to assess the influence of one heteroatom on the other in competition for an electrophile.The conditions of S-N, S-C, and N-C cleavage, and attack at sulfur as opposed to nitrogen, are described.