Abstract
[15296-86-3] C13H12O2S2 (MW 264.36) InChI = 1S/C13H12O2S2/c14-17(15,13-9-5-2-6-10-13)11-16-12-7-3-1-4-8-12/h1-10H,11H2 InChIKey = NRSIZSICNCVLJE-UHFFFAOYSA-N (reagent used as a one-carbon 1,1-dipole synthon with additional thiol-derived functional versatility) Physical Data: mp1 62–64 °C; ir (CDCl3)2 1140, 1320 cm−1, (KBr)1 1148(s), 1306(s), 1582(w), 2944(w), 3000(w), 3058(w) cm−1; 1H nmr1 (200MHz, CDCl3) δ 4.35 (s, 2H), 7.16–7.28 (m, 3H), 7.30–7.41 (m, 2H), 7.46–7.55 (m, 2H), 7.59–7.67 (m, 1H), 7.89–7.95 (m, 2H), and ms1 m/z (EI) 264 (M•C, 32.5%), 186 (14), and 123 (100); pKa (DMSO, 25 °C) 20.3.3 Solubility: common organic solvents. Preparative Methods: (a) oxidation of (PhS)2CH2 to PhSCH2SOPh with H2O2 in acetic acid, followed by KMnO4 oxidation;1 (b) oxidation of (PhS)2CH2 to PhSOCH2SO2Ph with H2O2 in acetic acid, followed by Zn/acetic acid reduction;4 (c) reaction of NaSPh or KSPh with BrCH2SO2Ph5 in DMF;6 (d) reaction of PhSCH2MgCl7 with PhSO2Cl.8 Purification: recrystallization from ether-petroleum ether.1
Published Version
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