CONVENIENT ONE-FLASK SYNTHESIS OF DIALKYL SELENIDES AND DISELENIDES VIA LITHIUM TRIETHYLBOROHYDRIDE REDUCTION OF SEX
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Commercially available Li(C2H5)3BH rapidly and quantitatively cleaves gray elemental Sex in THF to Li2Se or Li2Se2, depending upon stoichiometry. Only volatile byproducts (H2 and (C2H5)3B) are formed. The heterogeneous Li2Se and Li2Se2 preparations may be alkylated in 50-95% yield, optimally in the presence of tert-butyl alcohol co-solvent. This one-flask procedure constitutes a substantial improvement over conventional dialkyl selenide and dialkyl diselenide syntheses. Li(C2Hs)3BH (2 equiv) also effects reduction of diselenides to selenolates, which may be alkylated to give unsymmetrical selenides. 1978, American Chemical Society. All rights reserved.