Chemistry:Stibabenzene
Stibabenzene[1] is an organic chemical compound. Stibabenzene has the chemical formula C
5H
5Sb. 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 a molecule that 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.[2]
- C
5H
4 + Bu
2SnH
2 → C
13H
24Sn 
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.[1]
- C
13H
24Sn + SbCl
3 → C
5H
6SbCl 
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.
- C
5H
6SbCl + DBN → C
5H
6Sb 
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.[3]
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
- ↑ 1.0 1.1 Ashe, Arthur J. (December 1971). "Stibabenzene" (in EN). Journal of the American Chemical Society 93 (24): 6690–6691. doi:10.1021/ja00753a069. ISSN 0002-7863.
- ↑ Ashe, Arthur J.; Fang, Xiangdong; Fang, Xinggao; Kampf, Jeff W. (December 2001). "Synthesis of 1,2-Dihydro-1,2-azaborines and Their Conversion to Tricarbonyl Chromium and Molybdenum Complexes" (in en). Organometallics 20 (25): 5413–5418. doi:10.1021/om0106635. ISSN 0276-7333.
- ↑ Ashe, Arthur J. (February 2016). "The Route to Phosphabenzene and Beyond" (in en). European Journal of Inorganic Chemistry 2016 (5): 572–574. doi:10.1002/ejic.201600007. ISSN 1434-1948. https://deepblue.lib.umich.edu/bitstream/2027.42/117476/1/572_ftp.pdf.
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