Benzvalene
Encyclopedia
Benzvalene is an organic compound
and one of several isomer
s of benzene
.. It was synthesised in 1971 by Thomas J. Katz et al.
The 1971 synthesis consisted of treating cyclopentadiene
with methyllithium in dimethylether and then with dichloromethane
and methyllithium in at -45°C. The hydrocarbon in solution was described as having an extraordinary foul odor. Due to the high steric strain present in benzvalene, the pure compound easily detonates, for example by scratching.
The compound converts to benzene with a chemical half-life of approximately 10 days. This symmetry forbidden transition is believed to take place through a diradical intermediate
process to polybenzvalene . This polymer contains highly strained bicyclobutane rings which again makes it a sensitive material. The rings can be isomerized to 1,3-dienes and for this reason polybenzvalene has been investigated as a precursor to polyacetylene
.
Organic compound
An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...
and one of several isomer
Isomer
In chemistry, isomers are compounds with the same molecular formula but different structural formulas. Isomers do not necessarily share similar properties, unless they also have the same functional groups. There are many different classes of isomers, like stereoisomers, enantiomers, geometrical...
s of benzene
Benzene
Benzene is an organic chemical compound. It is composed of 6 carbon atoms in a ring, with 1 hydrogen atom attached to each carbon atom, with the molecular formula C6H6....
.. It was synthesised in 1971 by Thomas J. Katz et al.
The 1971 synthesis consisted of treating cyclopentadiene
Cyclopentadiene
Cyclopentadiene is an organic compound with the formula C5H6. This colorless liquid has a strong and unpleasant odor. At room temperature, this cyclic diene dimerizes over the course of hours to give dicyclopentadiene via a Diels–Alder reaction...
with methyllithium in dimethylether and then with dichloromethane
Dichloromethane
Dichloromethane is an organic compound with the formula CH2Cl2. This colorless, volatile liquid with a moderately sweet aroma is widely used as a solvent. Although it is not miscible with water, it is miscible with many organic solvents...
and methyllithium in at -45°C. The hydrocarbon in solution was described as having an extraordinary foul odor. Due to the high steric strain present in benzvalene, the pure compound easily detonates, for example by scratching.
The compound converts to benzene with a chemical half-life of approximately 10 days. This symmetry forbidden transition is believed to take place through a diradical intermediate
Polybenzvalene
Benzvalene can be polymerized in a ROMPRing opening metathesis polymerisation
Ring-opening metathesis polymerization is a type of olefin metathesis chain-growth polymerization that produces industrially important products. The driving force of the reaction is relief of ring strain in cyclic olefins and a wide variety of catalysts have been discovered...
process to polybenzvalene . This polymer contains highly strained bicyclobutane rings which again makes it a sensitive material. The rings can be isomerized to 1,3-dienes and for this reason polybenzvalene has been investigated as a precursor to polyacetylene
Polyacetylene
Polyacetylene is an organic polymer with the repeat unit n. The high electrical conductivity discovered for these polymers beginning in the 1960's accelerated interest in the use of organic compounds in microelectronics...
.