Arsabenzene

Arsabenzene (<a href="/facts/IUPAC/2AV6myCK">IUPAC</a> name: arsinine) is an <a href="/facts/Organoarsenic/BW425S1q">organoarsenic</a> <a href="/facts/Heterocyclic/8oYSjJxY">heterocyclic</a> compound with the chemical formula C5H5As. It belongs to a group of compounds called <a href="/facts/Heteroarene/dftWcLcL">heteroarenes</a> that have the general formula C5H5E (E= N, P, As, Sb, Bi).
This air sensitive liquid has an onion odor, and it decomposes on heating. Arsabenzene is also an <a href="/facts/Ambidentate_ligand/6etB3qeW">ambidentate ligand</a> that prefers to coordinate using η1(As)- or η6(π)-routes.
The study of arsabenzene and related compounds was an important step in the understanding of compounds that contain <a href="/facts/Multiple_bond/Tdb1zgTc">multiple bonds</a> between carbon and heavier elements. 
The study of heteroarenes was begun by Märkl, with the synthesis of 2,4,6-triphenylphosphabenzene. This is achieved by treating 2,4,6-trisubstituted <a href="/facts/Pyrylium_salt/QTplu8Ez">pyrylium salt</a> with <a href="/facts/Phosphane/aYysn5TS">phosphanes</a>. The first derivative of arsabenzene was 9-arsaanthracene prepared by Jutzi and Bickelhaupt.

Arsabenzene open-in-new

Arsabenzene