Arylstibanes

Arylstibanes are organostibane compounds in which one or more aryl groups are bonded directly to the antimony atom via Sb–C bonds. They include species such as triarylstibanes (for example Ph3Sb) and mixed aryl/alkyl derivatives (Ar2SbR, Ar3Sb, etc.). The Sb center in these compounds is typically trivalent and bears a lone pair, giving a pyramidal geometry that is common for many organoantimony(III) compounds. The Sb–C bonds are relatively covalent, and the compounds are generally sensitive to air and moisture.

Synthesis of arylstibanes is usually achieved by metathesis or transmetalation routes starting from aryl Grignard reagents or organolithiums and antimony halides or hydrides. A typical pathway involves reacting an aryl nucleophile (such as ArMgX or ArLi) with SbCl3 to form the corresponding Ar3Sb compound after workup. Alternative routes employ preformed arylstibine fragments or redistribution reactions among antimony centers.

Reactivity and properties: Arylstibanes are reactive toward oxidation, forming Sb(V) species, and can undergo ligand redistribution or transmetallation under suitable conditions. They are generally less common in routine synthesis than corresponding organoboron or organotin reagents but are studied as sources of aryl groups and as building blocks for more complex organoantimony chemistry. Their reactivity can be influenced by the nature of the aryl groups and additional substituents on antimony.

Applications and safety: In research settings, arylstibanes serve as reagents for aryl transfer and as precursors to other organoantimony compounds. They are moisture- and air-sensitive and must be handled under inert atmosphere. Antimony compounds can be toxic; appropriate containment, ventilation, and waste disposal are required. See also organoantimony chemistry and related organometallic families.

See also: organostibanes, organoantimony chemistry, organotin chemistry.