Stibabenzene[1] is an organicchemical 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.
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.
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]
File:Multiple Synthesis.pngThe four different reaction pathways possible from 1,1-dibutyl-1,4-dihydrostannin to form the products arsabenzene, phosphabenzene, bismabenzene, and stibabenzene.
↑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). Organometallics20 (25): 5413–5418. doi:10.1021/om0106635. ISSN0276-7333.
