Abstract
A convenient synthetic method has been developed for the preparation of unsymmetrical
selenides through a one-pot zinc-mediated reaction of diselenides and active organic
halides in aqueous media.
Key words
diselenides - selenides - zinc - zinc selenolate - halides
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General Experimental Procedure. In a 50 mL round-bottom flask, fitted with a reflux condenser, were placed zinc powder
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diselenide, AlCl3 (1.5 mmol) was also added at this stage.) The mixture was stirred at 65 °C for 1
h until the zinc powder was almost consumed and the solution became turbid; organic
halide (1.8 mmol) and H2 O (2 mL) were then added at once to the solution and stirring was continued for the
specified time (Table
[1 ]
) at 65 °C. Progress of the reaction was monitored by TLC. When the reaction was complete,
MeCN was evaporated, Et2 O (30 mL) was added, the mixture washed with H2 O (3 × 20 mL), and the organic layer was dried over anhyd Na2 SO4 . The solvent was evaporated in vacuo to give the corresponding selenide which was
purified by preparative TLC (silica gel, eluent petroleum ether-CCl4 = 1:1 or petroleum ether-Et2 O = 9:1 or CCl4 -Et2 O = 4:1).
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