Samarium (II) diiodide‐induced reductive cleavage of SeSe and TeTe bond in diphenyl diselenide and ditelluride leading to a samarium phenylselenolate and tellurolate: Preparation of unsymmetrical alkylphenyl selenides and tellurides

Diphenyl diselenide and diphenyl ditelluride were reduced by samarium (II) diiodide in tetrahydrofuran-hexamethylphosphoric triamide to produce samarium phenylselenolate and samarium phenyltellurolate, respectively. This new selenolate or tellurolate anion species reacted smoothly with alkyl, allyl, and benzyl halides to give alkyl-, allyl-, and benzylphenyl selenides or tellurides in good yields under mild and neutral conditions. The samarium selenolate reacted with α-halo ketones to give the corresponding α-phenylseleno ketones. 1,4-Addition with α,β-enones proceeded to give 3-phenylseleno ketones in moderate yields. Isolation of phenylselenotributyltin or phenylseleno-trimethylsilane by transmetalation with tributyltin iodide or trimethylchlorosilane, respectively, suggested the presence of the samarium selenolate species.