Organic Diselenides from Organic Halides
2691
General Procedure for the Synthesis of Organic Diselenides
In a 100-mL, three-necked flask, organic halide (2.5 mmol), selenium
(2.5 mmol), water (2 mL), sodium hydroxide (2.5 mmol), DMF (20 mL),
and a magnetic stirring bar were placed. Carbon monoxide was introduced
and bubbled into the reaction mixture with vigorous stirring at 908C for 2 h.
After the reaction was complete, CO bubbling was stopped, and the
resultant mixture was stirred in air at ambient temperature for 0.5 h.
Water (20 mL) was added, and the reaction mixture was extracted with
diethyl ether (3 ꢁ 40 mL). The organic phase was dried over anhydrous
MgSO4 and filtered, and the solvent evaporated under reduced pressure to
afford a yellow oil or crystal. Further purification by column chromato-
graphy on silica gel or recrystallization gave the pure product. All the
products were identified by NMR and/or comparison with the authentic
samples.
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