The reaction of a dipotassium silyl dianion (1) with chalcogenide elements (E) does not afford the corresponding silylchalcogenolates, but allows the generation of a series of heterocyclic disilylchalcogenides (E = S (2), Se (3), Te (4)). Under high temperature, compound 4 can be converted into compound 5, a Te analog of compounds 2 and 3. The compounds were characterized by (1)H, (13)C and (29)Si NMR spectroscopy and high resolution mass spectrometry (HRMS). In addition, X-ray structure analyses were carried out on compounds 2-5. A DFT calculation was also performed.