Stannole is an
organotin compound
Organotin chemistry is the scientific study of the synthesis and properties of organotin compounds or stannanes, which are organometallic compounds containing tin–carbon bonds. The first organotin compound was diethyltin diiodide (), discovered ...
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 ...
(
C H)
4 SnH
2. 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 ...
, i.e. an unsaturated five-membered ring containing a
heteroatom
In chemistry, a heteroatom () is, strictly, any atom that is not carbon or hydrogen.
Organic chemistry
In practice, the term is mainly used more specifically to indicate that non-carbon atoms have replaced carbon in the backbone of the molecular ...
. It is 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 ...
of
cyclopentadiene
Cyclopentadiene is an organic compound with the chemical formula, formula C5H6. It is often abbreviated CpH because the cyclopentadienyl anion is abbreviated Cp−.
This colorless liquid has a strong and unpleasant odor. At room temperature, ...
, with
tin
Tin is a chemical element; it has symbol Sn () and atomic number 50. A silvery-colored metal, tin is soft enough to be cut with little force, and a bar of tin can be bent by hand with little effort. When bent, a bar of tin makes a sound, the ...
replacing the saturated
carbon
Carbon () is a chemical element; it has chemical symbol, symbol C and atomic number 6. It is nonmetallic and tetravalence, tetravalent—meaning that its atoms are able to form up to four covalent bonds due to its valence shell exhibiting 4 ...
atom. Substituted derivatives, which have been synthesized, are also called stannoles.
Examples
1,1-Dibutylstannole is a pale yellow oil prepared from 1,4-dilithio-1,3-butadiene and dibutyltin dichloride.
:
1,1-Dimethyl-2,3,4,5-tetraphenyl-1''H''-stannole, for example, can be formed by the
displacement reaction of 1,4-dilithio-1,2,3,4-tetraphenyl-1,3-butadiene and
dimethyltin dichloride.
[
]
1,1-Disubstituted stannoles can be formed in the
+2+1cycloaddition reaction
In organic chemistry, a cycloaddition is a chemical reaction in which "two or more unsaturated molecules (or parts of the same molecule) combine with the formation of a cyclic adduct in which there is a net reduction of the bond multiplicity". T ...
of two
acetylene
Acetylene (Chemical nomenclature, systematic name: ethyne) is a chemical compound with the formula and structure . It is a hydrocarbon and the simplest alkyne. This colorless gas is widely used as a fuel and a chemical building block. It is u ...
molecules with an
organotin
Organotin chemistry is the scientific study of the synthesis and properties of organotin compounds or stannanes, which are organometallic compounds containing tin–carbon bonds. The first organotin compound was diethyltin diiodide (), discove ...
molecule SnR
2.
[
]
Related compounds
1λ
2-Stannole has formula C
4H
4Sn, with no hydrogen on the tin atom, which is in the +2 oxidation state.
See also
*
Organotin chemistry
Organotin chemistry is the scientific study of the synthesis and properties of organotin compounds or stannanes, which are organometallic compounds containing tin–carbon bonds. The first organotin compound was diethyltin diiodide (), discove ...
References
{{Reflist
Tin heterocycles
Metalloles
Tin(IV) compounds