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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].

AdductsEdit

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

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The pyridine adduct Template:Chem is structurally related to biphenyl.<ref>Template:Cite journal</ref> 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.

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Adducts of borabenzene with pyridine and triphenylphosphine.
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The borabenzene-pyridine adduct behaves like a diene, not an analog of biphenyl, and will undergo Diels-Alder reactions.<ref>Template:Cite journal</ref>

Borabarrelene synthesis via a Diels-Alder reaction of borabenzene-pyridine adduct

See alsoEdit

ReferencesEdit

<references/>Template:Boron heterocycles