Stibabenzene
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 chloride can yield
arsabenzene,
Phosphorine, 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
