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Stibinin, also known as stibabenzene, is an
The second step of the synthesis involves reacting the product of the first step, 1,1-dibutyl-1,4-dihydrostannine, with antimony trichloride, to yield 1-chloro-1-stibacyclohexa-2,5-diene.
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The final step of the synthesis of stibinin involves treating 1-chloro-1-stibacyclohexa-2,5-diene with a base, such as DBN, to yield the final product of stibinin.
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organic
Organic may refer to:
* Organic, of or relating to an organism, a living entity
* Organic, of or relating to an anatomical organ
Chemistry
* Organic matter, matter that has come from a once-living organism, is capable of decay or is the product ...
chemical compound. Stibinin has the chemical formula . The molecule, stibinin, is a derivative of benzene, with one of the carbon atoms in the 6-membered ring replaced by an antimony (Sb) atom. Stibinin is a molecule that is considered to be an organoantimony compound due to it containing carbon, hydrogen, and antimony atoms.
Laboratory synthesis
The synthesis of stibinin can be accomplished in a three step process. The final product can be isolated, even though the molecule is highly labile. The first step of this synthesis involves the treatment ofpenta-1,4-diyne
1,4-Pentadiyne (penta-1,4-diyne) is a chemical compound belonging to the alkynes. The compound is the structural isomer to 1,3-pentadiyne. Preparation
Until the late 1960s, no successful synthesis of this seemingly simply preparable molecule wa ...
with dibutylstannane as shown in the figure below.
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The second step of the synthesis involves reacting the product of the first step, 1,1-dibutyl-1,4-dihydrostannine, with antimony trichloride, to yield 1-chloro-1-stibacyclohexa-2,5-diene.
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The final step of the synthesis of stibinin involves treating 1-chloro-1-stibacyclohexa-2,5-diene with a base, such as DBN, to yield the final product of stibinin.
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Similar compounds
It is noted that other benzene derivatives with one carbon replaced with a group 15 element can be synthesized via a similar synthetic pathway to that which stibinin is synthesized. The reaction of 1,1-dibutyl-1,4-dihydrostannine with arsenic trichloride, phosphorus tribromide, orbismuth trichloride
Bismuth chloride (or butter of bismuth) is an inorganic compound with the chemical formula BiCl3. It is a covalent compound and is the common source of the Bi3+ ion. In the gas phase and in the crystal, the species adopts a pyramidal structure, i ...
can yield arsabenzene, phosphabenzene, or 1-chloro-1-bismacyclohexa-2,5-diene respectively. Treatment of 1-chloro-1-bismacyclohexa-2,5-diene with a base, such as DBN, can yield the product bismabenzene
Bismabenzene () is the parent representative of a group of organobismuth compounds that are related to benzene with a carbon atom replaced by a bismuth atom. Bismabenzene itself has been synthesised but not isolated because it is too reactive, te ...
.
See also
* 6-membered aromatic rings with one carbon replaced by another group: borabenzene, silabenzene, germabenzene, stannabenzene, pyridine,phosphorine
Phosphorine ( IUPAC name: phosphinine) is a heavier element analog of pyridine, containing a phosphorus atom instead of an aza- moiety. It is also called phosphabenzene and belongs to the phosphaalkene class. It is a colorless liquid that is ...
, arsabenzene, stibabenzene, bismabenzene
Bismabenzene () is the parent representative of a group of organobismuth compounds that are related to benzene with a carbon atom replaced by a bismuth atom. Bismabenzene itself has been synthesised but not isolated because it is too reactive, te ...
, pyrylium, thiopyrylium, selenopyrylium
Selenopyrylium is an aromatic heterocyclic compound consisting of a six-membered ring with five carbon atoms and a positively charged selenium atom.
Naming and numbering
Formerly it was named selenapyrylium. However, this is misleading as "selena ...
, telluropyrylium
Telluropyrylium is an aromatic heterocyclic compound consisting of a six member ring with five carbon atoms, and a positively charged tellurium atom. Derivatives of telluropyrylium are important in research of infrared dyes.
Naming and numbering
...
References
{{Reflist Antimony heterocycles