14cyclohexadiene

14Cyclohexadiene is a name sometimes used to denote 1,4-cyclohexadiene, a non-aromatic hydrocarbon with the formula C6H8. It consists of a six-membered ring bearing two isolated carbon–carbon double bonds at positions 1–2 and 4–5.

Structure and properties: In 1,4-cyclohexadiene, the two double bonds are not conjugated, and the ring can adopt several conformations, including chair- and boat-like forms. The molecule is nonplanar overall due to the geometry of the cyclohexane ring, and it lacks aromatic stabilization. It is typically less conjugated and less reactive as a diene compared with conjugated isomers such as 1,3-cyclohexadiene.

Synthesis and occurrence: 1,4-Cyclohexadiene is not a common bulk material and is usually prepared or generated in situ for research purposes, often by dehydrogenation or elimination routes from suitable precursors. Because it is a hydrocarbon with modest stability, it is commonly handled under controlled conditions and, when isolated, is typically studied as a reactive intermediate or in the context of fundamental organic chemistry.

Reactions: The compound reacts in typical alkene fashion, undergoing hydrogenation to give cyclohexene or cyclohexane, and adding reagents across its double bonds. Under certain conditions, it can isomerize to the conjugated 1,3-cyclohexadiene, which may exhibit different reactivity and stability. Its chemical use is mainly as a reference system for understanding ring strain, conformational effects, and isomerization processes in cyclohexadienes.

See also: 1,3-cyclohexadiene, 1,4-cyclohexadiene isomerism, cyclohexadiene chemistry.