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Representative Procedure for the Preparation of (3Z, 4-Chloro-3, Z)-2-chloro-1-(1-hydroxy-1-methylethyl)vinyl]selanyl, 2-methylbut-3-en-2-ol (1e) The THF solution of selenium dichloride (1 mmol) prepared by the known procedure3 was added dropwise to a solution of 2-methylbut-3-yn-2-ol (172 mg, 2 mmol) in dry THF (2 mL) at 0°C. Then the reaction mixture was stirred at r.t. for 35 min. After completion of the reaction (TLC, the reaction mixture was extracted with EtOAc (20 mL) and washed with H2O (5 mL) and brine (2 x 5 mL, The organic layer was dried over Mg2SO4. After evaporation of the solvent the crude product, containing 92% of selenide 1e and 8% of diselenide 2e, was obtained. After column chromatography with silica gel (hexanes-EtOAc, 4:1) pure 1e was obtained 264 mg, 82% yield
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4. After evaporation of the solvent the crude product, containing 92% of selenide 1e and 8% of diselenide 2e, was obtained. After column chromatography with silica gel (hexanes-EtOAc, 4:1) pure 1e was obtained (264 mg, 82% yield).
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Analytical and Spectroscopic Data for Representative Compounds (2Z)-3-Chloro-2, Z)-2-chloro-1-(hydroxymethyl) vinyl]selanyl}prop-2-en-1-ol (1a) Viscous liquid. IR (neat, 3453 (br, 2972, 1571, 1368, 1169, 1129, 980 cm-1. 1H NMR (600 MHz, CDCl3, δ, 3.62 (br s, 2 H, OH, 4.46 (d, 4 H, J, 1.1 Hz, 6.55 (t, 2 H, J, 1.1 Hz, 13C NMR (150 MHz, δ, 60.9 (CH2, 122.2 (CH, 2JC,Se, 22.6 Hz, 132.8 (C, 1JC,Se, 112.6 Hz, HRMS: m/z calcd for C6H8Cl2O278Se: 259.9074; found: 259. 9058, 2Z)-3-Chloro-2, 1 Z)-2-chloro-1-(hydroxy methyl)prop-1-enyl]selanyl}but-2-en-1-ol (1b) Solid, mp 56-58°C. IR (KBr, 3324 (br, 2976, 1606, 1455. 1015 cm-1. 1H NMR 600 MHz, CDCl3, δ, 2.4
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C,Se = 15.9 Hz).
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