What is a barrelene?

Barrelene is a name used to describe various barrel-shaped hydrocarbons. It usually specifically refers to the class of aromatic compounds related to benzene in which two diametrically opposed -CH= groups have been added to the benzene ring. It is classified as a polycyclic aromatic hydrocarbon (PAH).

Structure

Barrelene has the chemical formula C10H10. Barrelene's structure is similar to cyclobutadiene, but it is more stable due to the presence of two additional double bonds. The barrelene molecule consists of a six-membered carbon ring with two opposite carbon atoms replaced by carbon-carbon double bonds. The resulting structure resembles a barrel, hence the name "barrelene".

Synthesis

Barrelene was first synthesized in 1962 by the German chemist Wilhelm Tochtermann and his team. It can be synthesized by a variety of methods, including the reaction of dicyclopentadiene with iodine.

Properties

Barrelene is a colorless liquid at room temperature. It has a boiling point of 198 °C and a melting point of -78 °C. Barrelene is soluble in organic solvents, such as benzene and ether.

Reactivity

Barrelene is a reactive hydrocarbon. It undergoes a variety of reactions, including addition reactions, substitution reactions, and cycloadditions. Barrelene can also be used as a ligand for metal ions.

Applications

Barrelene is a valuable research tool in organic chemistry. It has also been used as a precursor for the synthesis of other more complex organic compounds.

Conclusion

Barrelene is a fascinating and versatile organic compound with a unique structure and reactivity. It has been the subject of numerous research studies and has applications in a variety of fields.