Stibabenzene

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 atom. Stibabenzene is a molecule that is considered to be an organoantimony compound due to it containing carbon, hydrogen, and antimony atoms.
File:Bond lengths of group 15 heterobenzenes and benzene.svg|thumb|center|upright=2|Bond lengths and angles of benzene, pyridine, phosphorine, arsabenzene, stibabenzene, and bismabenzene

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.