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Cyclic silylated chalconium borates 13[B(C6F5)4] and 14[B(C6F5)4] with peri‐acenaphthyl and peri‐naphthyl skeletons were synthesized from unsymmetrically substituted silanes 3, 4, 6, 7, 9 and 10 using the standard Corey protocol (Chalcogen Ch=O, S, Se, Te). The configuration at the chalcogen atom is trigonal pyramidal for Ch=S, Se, Te, leading to the formation of cis‐ and trans‐isomers in the case...