Cyclohexa-1,4-diene

It is a colourless, flammable liquid that is of academic interest as a prototype of a large class of related compounds called terpenoids, an example being γ-terpinene.

In the laboratory, substituted 1,4-cyclohexadienes are synthesized by Birch reduction of related aromatic compounds using an alkali metal dissolved in liquid ammonia and a proton donor such as an alcohol.

In this way, over reduction to the fully saturated ring is avoided.

1,4-Cyclohexadiene and its derivatives are easily aromatized, the driving force being the formation of an aromatic ring.

The conversion to an aromatic system may be used to trigger other reactions, such as the Bergman cyclization.

Skeletal formula with all implicit hydrogen shown, skeletal formula; stereo, skeletal formula with all explicit hydrogens added, all of 1,4-cyclohexadiene
Skeletal formula with all implicit hydrogen shown, skeletal formula; stereo, skeletal formula with all explicit hydrogens added, all of 1,4-cyclohexadiene
1,4-Cyclohexadiene molecule
1,4-Cyclohexadiene molecule
NFPA 704 four-colored diamond Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform Flammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasoline Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen Special hazards (white): no code