Electrochemical investigation of the chloroselenobenzene under its atmosphere-sensitive characteristics

•Electro-reduction and -oxidation of chloroselenobenzene was led to synthesis of new diselenol, diselenide, and polyselenide.•Electro-reduction of chloroselenobenzene produced diselenide (under N2 atmosphere) or a polyselenide (under air atmosphere)•The electrolysis was carried out in a simple cell, under simple conditions, without using any catalysts. Electrochemical oxidation and reduction of the chloroselenobenzene were described in a catalyst-less and mild solution through cyclic voltammetry and controlled-potential electrolysis under air and nitrogen atmosphere. By electrogenerated intermediates and controlling conditions, unique compounds, including a Diselenol, Diselenide, and Polyselenid, were synthesized in good to excellent yields and purities. These compounds can be oxidized at the surface of the carbon electrode to produce reactive precursors with several Michael addition positions for further investigations. [Display omitted]