Borabenzene

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]−.

Borabenzene
Names
Other names
Borinine
Identifiers
3D model (JSmol)
ChemSpider
Properties
C5H5B
Molar mass 75.91 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Adducts
Adducts of borabenzene with pyridine and triphenylphosphine.

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

C5H5N + MeOBC5H5SiMe3 → C5H5N-BC5H5 + MeOSiMe3

The pyridine adduct C5H5N-BC5H5 is structurally related to biphenyl.[1] It is a yellow solid. The pyridine ligand is tightly bound: no exchange is observed with deuterated pyridine at elevated temperatures.

The borabenzene-pyridine adduct behaves like a dienes, not an analogue of biphenyl.[2]

See also

References
  1. Boese, Roland; Finke, Norbert; Henkelmann, Jochem; Maier, Günther; Paetzold, Peter; Reisenauer, Hans Peter; Schmid, Günter (1985). "Synthese und Strukturuntersuchung von Pyridin-Borabenzol und Pyridin-2-Boranaphthalin". Chemische Berichte. 118 (4): 1644–1654. doi:10.1002/cber.19851180431.
  2. Wood, Thomas K.; Piers, Warren E.; Keay, Brian A.; Parvez, Masood (2006). "1-Borabarrelene Derivatives via Diels−Alder Additions to Borabenzenes". Organic Letters. 8 (13): 2875–2878. doi:10.1021/ol061201w. PMID 16774279.
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