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9
4-(4-Chlorophenylseleno)butan-2-one - Typical Procedure
In a typical experiment, a mixture of bis(4-chloro-phenyl)diselenide (190 mg, 0.5 mmol), zinc dust (229 mg, 3.5 mmol), and ruthenium(III) chloride hydrate (13 mg, 0.05 mmol) was suspended in MeCN (8 mL) and H2O (2 mL). The mixture was stirred at 80 °C for 1.5 h, during which time the zinc powder was almost completely consumed. Then, methyl vinyl ketone (73 mg, 1.05 mmol) was added at once to the mixture and stirring was continued at that temperature for 1 h in air. After completion of the reaction, the solution was filtered, the solvent was evaporated, and the residue was subjected to preparative TLC (silica gel, eluent, n-hexane-EtOAc = 4:1) to afford pure 4-(4-chlorophenylseleno)butan-2-one (255 mg, 98%, Table
[1]
, entry 11) as a pale yellow oil. IR (neat): 1720, 1478, 739 cm-1. 1H NMR (300 MHz, CDCl3): δ = 2.14 (s, 3 H), 2.84 (t, 2 H, J = 7.2 Hz), 3.05 (t, 2 H, J = 7.2 Hz), 7.25 (d, 2 H, J = 8.5 Hz), 7.42 (d, 2 H, J = 8.5 Hz) ppm. 13C NMR (75 MHz, CDCl3): δ = 20.8, 30.0, 43.9, 127.9, 129.3, 133.3, 134.3, 206.8 ppm. MS: m/z (%) = 264 (46) [(M + 4]+ , 262 (90) [M + 2]+, 260 (49) [M+], 219 (15), 191 (20), 151 (24), 71 (55), 43 (100). Anal. Calcd for C10H11ClOSe: C, 45.91; H, 4.24. Found: C, 46.30; H, 4.51.
Spectroscopic Data for Entry 12, Table 1
IR (neat): 1710, 1478, 738 cm-1. 1H NMR (500 MHz, CDCl3): δ = 2.13 (s, 3 H), 2.69-2.71 (m, 2 H), 2.74-2.77 (m, 2 H), 3.84 (s, 2 H), 7.24-7.33 (m, 5 H) ppm. 13C NMR (125 MHz, CDCl3): δ = 17.0, 28.1, 30.4, 44.7, 127.2, 128.9, 129.3, 139.7, 207.6 ppm. MS: m/z (%) = 242 (30) [M + 2]+, 240 (16) [M+], 181 (10), 91 (100), 65 (22), 43 (51). Anal. Calcd for C11H14OSe: C, 54.78; H, 5.85. Found: C, 54.51; H, 5.64.