Stibabenzene is an 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 (Sb) atom. Stibabenzene is considered to be an 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 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 trichloride 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.
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
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