Borabenzene

 ( Boron Heterocycles ) 

Borabenzene is a hypothetical organoboron compound with the formula C₅H₅B. Unlike the related but highly stable benzene molecule, borabenzene would be electron-deficient. Related derivatives are the boratabenzene anions, including the parent C₅H₅BH⁻.

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Adducts Adducts of borabenzene with are isolatable. Since borabenzene is unavailable, these adducts require indirect methods. 4-Silyl-1-methoxyboracyclohexadiene is used as a precursor to the borabenzene:

+ → + MeOSiMe₃

The pyridine adduct is structurally related to biphenyl. It is a yellow whereas biphenyl is colorless, indicating distinct electronic structures. The pyridine ligand is tightly bound: no exchange is observed with free pyridine, even at elevated temperatures.

The borabenzene-pyridine adduct behaves like a diene, not an analog of biphenyl, and will undergo Diels-Alder reactions.

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See also

• 6-membered aromatic rings with one carbon replaced by another group: silabenzene, germabenzene, stannabenzene, pyridine, phosphorine, arsabenzene, stibabenzene, bismabenzene, pyrylium, thiopyrylium, selenopyrylium, telluropyrylium
• Borazine

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