Cyclobutadiene Dianion

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  • Award Accounts: The Chemical Society of Japan Award for Young Chemists for 2002
  • Award Accounts The Chemical Society of Japan Award for Young Chemists for 2002

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<jats:title>Abstract</jats:title> <jats:p>In this account, we present the synthesis and chemistry of the dilithium salts of the cyclobutadiene dianion (CBD2−), which contains a doubly charged four-membered ring system. The transmetalation reaction of tetrasilyl-substituted cyclobutadiene (CBD) cobalt complexes (5,6) with lithium metal led to the formation of the corresponding dilithium salts of CBD2− (10,11). The aromaticity of the CBD2− species has been studied on the basis of structural characteristics and magnetic properties. The dilithium salts of CBD2− stabilized by both phenyl and silyl groups (12–14) were also prepared by a similar procedure, starting from the corresponding CBD cobalt complexes (7–9). The CBD2− species have been fully characterized by NMR studies and X-ray crystallography. The two-electron oxidation reaction of the tetrasilyl-CBD2− (10,11) with 1,2-dibromoethane produced the neutral CBD derivatives (17,22). The structures, properties, and reactivities of the tetrasilyl-substituted CBD are also reviewed here. Tetrakis(trimethylsilyl)tetrahedrane (26) was synthesized by irradiation of tetrakis(trimethylsilyl)cyclobutadiene (17). The structure and properties of tetrahedrane (26) are presented.</jats:p>

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