Cyclohexa-1,4-diene

Cyclohexa-1,4-diene
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Abbreviations	1,4-CHDN
Template:Longitem	1900733
ChEBI	Template:Unbulleted list
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EC Number	Template:Unbulleted list
Template:Longitem	1656
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MeSH	1,4-cyclohexadiene
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RTECS number	Template:Unbulleted list
UN number	3295
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Template:Longitem	Template:Chembox Elements/molecular formula
Molar mass	Template:Chem molar mass
Appearance	Colorless liquid
Density	0.847 g cm−3
Melting point	Template:Chembox CalcTemperatures
Boiling point	Template:Chembox CalcTemperatures
Template:Longitem	−48.7·10−6 cm3/mol
Template:Longitem	1.472
Template:Longitem	142.2 J K−1 mol−1
Template:Longitem	189.37 J K−1 mol−1
Template:Longitem	63.0–69.2 kJ mol−1
Template:Longitem	−3573.5 – −3567.5 kJ mol−1

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1,4-Cyclohexadiene is an organic compound with the formula C₆H₈. 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. An isomer of this compound is 1,3-cyclohexadiene.

Synthesis and reactions

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.Script error: No such module "Unsubst". Alternatively, 1,4-cyclohexadienes are the Diels-Alder product of butadiene and an electron-poor alkyne.^[2]

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.^[3]

References

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↑ John C. Walton, Fernando Portela-Cubillo "1,4-Cyclohexadiene" Encyclopedia of Reagents for Organic Synthesis 2007 John Wiley & Sons. Script error: No such module "CS1 identifiers".

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External links

The photochemistry of 1,4-cyclohexadiene in solution and in the gas phase
NIST Chemistry WebBook Reaction thermochemistry data

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[1] Script error: No such module "citation/CS1".

[2] Script error: No such module "Citation/CS1".

[3] John C. Walton, Fernando Portela-Cubillo "1,4-Cyclohexadiene" Encyclopedia of Reagents for Organic Synthesis 2007 John Wiley & Sons. Script error: No such module "CS1 identifiers".

[2]

[3]

Cyclohexa-1,4-diene

Synthesis and reactions

References

External links

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