Synthesis, structure and redox property of first 1,2,3-triselenole

Photolysis of [Fe3Se2(CO)9] with 3-ferrocenylpropynal in hexane yields an adduct of [Fe2Se2(CO)6] and FcC2CHO, [(CO)6Fe2{μ-SeC(Fc)C(CHO)Se}] (1). Subsequent reaction of 1 with [Fe2Se2(CO)6] in presence of excess of Me3NO·2H2O in THF leads to formation of a novel 5-ferrocenyl-4-carbaldehyde-1,2,3-triselenole (2). Its electrochemistry has been investigated by cyclic voltammetry, which shows two successive quasi-reversible oxidations.

Synthesis of first unfused triselenole is shown by reaction of adduct [(CO)6Fe2{μ-SeC(Fc)C(CHO)Se}], formed by photolysis of Fe3(μ-Se2)(CO)9 and FcC2CHO, with Fe2(μ-Se)2(CO)6 in presence of Me3NO·2H2O.Figure optionsDownload as PowerPoint slideHighlights
► Facile method for synthesis of the first unfused 5-ferrocenyl-4-carbaldehyde-1,2,3-triselenole.
► Reaction of [(CO)6Fe2{μ-SeC(Fc)C(CHO)Se}] adduct with Fe2(μ-Se2)(CO)6 in presence of TMNO·2H2O.
► Two successive quasi-reversible oxidations.