Stibole is a theoretical

heterocyclic A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its ring(s). Heterocyclic organic chemistry is the branch of organic chemistry dealing with the synthesis, proper ...

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

, a five-membered ring with the

formula In science, a formula is a concise way of expressing information symbolically, as in a mathematical formula or a ''chemical formula''. The informal use of the term ''formula'' in science refers to the general construct of a relationship betwe ...

C₄ H₄ SbH. It is classified as a

metallole Metalloles are metallacycle derivatives of cyclopentadiene in which the carbon atom at position 5, the saturated carbon, is replaced by a heteroatom. In contrast to its parent compound, the numbering of the metallole starts at the heteroatom. Some ...

. It can be viewed as a

structural analog A structural analog, also known as a chemical analog or simply an analog, is a chemical compound, compound having a chemical structure, structure similar to that of another compound, but differing from it in respect to a certain component. It can ...

pyrrole Pyrrole is a heterocyclic, aromatic, organic compound, a five-membered ring with the formula . It is a colorless volatile liquid that darkens readily upon exposure to air. Substituted derivatives are also called pyrroles, e.g., ''N''-methylpyrrol ...

, with antimony replacing the

nitrogen Nitrogen is a chemical element; it has Symbol (chemistry), symbol N and atomic number 7. Nitrogen is a Nonmetal (chemistry), nonmetal and the lightest member of pnictogen, group 15 of the periodic table, often called the Pnictogen, pnictogens. ...

atom of pyrrole. Stibole itself is very rare, but many substituted derivatives have been synthesized. They are called stiboles.

Reactions

Pentaphenylstibile is prepared from 1,4-dilithio-1,2,3,4-tetraphenylbutadiene and phenylantimony dichloride by a

salt metathesis reaction A salt metathesis reaction (also called a double displacement reaction, double replacement reaction, or double decomposition) is a type of chemical reaction in which two ionic compounds in aqueous solution exchange their component ions to form two ...

: : (Ph = C₆H₅) 2,5-Dimethyl-1-phenyl-1''H''-stibole, for example, can be formed by the reaction of 1,1-dibutyl-2,5-dimethyl

stannole Stannole is an organotin compound with the chemical formula, formula (carbon, Chydrogen, H)4tin, SnH2. It is classified as a metallole, i.e. an unsaturated five-membered ring containing a heteroatom. It is a structural analog of cyclopentadiene, ...

and dichlorophenylstibine. Stiboles can be used to form

ferrocene Ferrocene is an organometallic chemistry, organometallic compound with the formula . The molecule is a Cyclopentadienyl complex, complex consisting of two Cyclopentadienyl anion, cyclopentadienyl rings sandwiching a central iron atom. It is an o ...

-like

sandwich compound In organometallic chemistry, a sandwich compound is a chemical compound featuring a metal bound by hapticity, haptic, covalent bonds to two arene compound, arene (ring) ligands. The arenes have the formula , substituted derivatives (for example ...

References

Antimony heterocycles Metalloles Hypothetical chemical compounds {{theoretical-chem-stub

Reactions

See also

References