Stibinin Reaction Schematic 3
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Stibabenzene is an Organic compound, organic chemical compound. Stibabenzene has the chemical formula . The molecule is a derivative of benzene, with one of the carbon atoms in the 6-membered ring replaced by an Antimony, antimony (Sb) atom. Stibabenzene is a molecule that is considered to be an Organoantimony chemistry, organoantimony compound due to it containing carbon, hydrogen, and antimony atoms.


Laboratory synthesis

The synthesis of stibabenzene 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 of penta-1,4-diyne with dibutylstannane as shown in the figure below. : : 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. : : The final step of the synthesis of stibabenzene involves treating 1-chloro-1-stibacyclohexa-2,5-diene with a base, such as 1,5-Diazabicyclo(4.3.0)non-5-ene, DBN, to yield the final product of stibabenzene. : :


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 stibabenzene is synthesized. The reaction of 1,1-dibutyl-1,4-dihydrostannine with arsenic trichloride, phosphorus tribromide, or Bismuth chloride, bismuth trichloride can yield arsabenzene, Phosphorine, phosphabenzene, or 1-chloro-1-bismacyclohexa-2,5-diene respectively. Treatment of 1-chloro-1-bismacyclohexa-2,5-diene with a base, such as 1,5-Diazabicyclo(4.3.0)non-5-ene, DBN, can yield the product bismabenzene.


See also

* 6-membered aromatic rings with one carbon replaced by another group: borabenzene, silabenzene, germabenzene, stannabenzene, pyridine, phosphorine, arsabenzene, stibabenzene, bismabenzene, pyrylium, thiopyrylium, selenopyrylium, telluropyrylium


References

{{Reflist Antimony heterocycles Six-membered rings