Ketene Dimethyl Thioacetal Monoxide

[111674-84-1] C4H8OS2 (MW 136.26) InChI = 1S/C4H8OS2/c1-4(6-2)7(3)5/h1H2,2-3H3 InChIKey = XGVUDALAYNWCJV-UHFFFAOYSA-N (formylmethyl synthon used as an acceptor in conjugate addition reactions1) Alternate Names: ketene bis(methylthio)acetal monoxide; 1-(methylsulfinyl)-1-methylthioethylene. Physical Data: yellow liquid; bp 145–150 °C/27 mmHg; 1H NMR (CDCl3) δ 2.38 (3H, s), 2.64 (3H, s), 5.51 (1H, d, J = 2 Hz), 6.01 (1H, d, J = 2 Hz); IR (neat) 3490, 1593, 1429, 1330, 1070, 970, 893 cm−1; MS (70 eV), m/e (rel. intensity) 136 (5.9, M+), 126 (0.8), 120 (1.6), 108 (3.2), 90 (8.4), 73 (100.0), 58 (15.1).2 Solubility: sol most common organic solvents (i.e. THF, Et2O, DME, CH2Cl2, MeCN, t-BuOH, CS2, benzene). Preparative Methods: prepared from glyoxylic acid in six steps.1a A shorter synthesis involving a two-pot reaction sequence has been developed.2 Recently, oxidation of methyl ethanedithioate with N-sulfonyloxaziridine in the presence of a base followed by alkylation with iodomethane afforded the reagent in a good yield.7