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Norbornadiene
 
 
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Norbornadiene is a bicyclic hydrocarbon
Hydrocarbon

In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. With relation to chemical terminology, aromatic hydrocarbons or arenes, alkanes, alkenes and alkyne-based compounds composed entirely of carbon or hydrogen are referred to as "pure" hydrocarbons, whereas other hydrocarbons with bonded com...
. The molecule can be envisioned as a 1,4-cyclohexadiene bridged in the para positions by a methylene
Methylene

Methylene is the chemical species, R2C:, named after methane, in which two of the carbon atom's valence electrons form no bonds. The word is applicable to:...
 group. The compound is related to norbornene
Norbornene

Norbornene or norbornylene or norcamphene is a bridged cyclic hydrocarbon. It is a white solid with a pungent sour odor. The molecule consists of a cyclohexene ring bridged with a methylene group in the arene substitution patterns....
 in which one of the double bonds is saturated
Saturation (chemistry)

In chemistry, saturation has five different meanings:#In physical chemistry, saturation is the point at which a solution of a substance can dissolve no more of that substance and additional amounts of it will appear as a Precipitation ....
. Norbornadiene and related compounds are of great scientific interest because of the unusual geometry and high reactivity.

norbornadiene framework is based on a Diels-Alder reaction
Diels-Alder reaction

The Diels-Alder reaction is an organic chemical reaction between a conjugated diene and a substituted alkene, commonly termed the dienophile, to form a substituted cyclohexene system....
 between a cyclopentadiene
Cyclopentadiene

Cyclopentadiene is a chemical compound with the Chemical formula C5H6. This colorless liquid organic chemistry chemical compound has a strong and unpleasant odor....
 and an alkyne
Alkyne

Alkynes are hydrocarbons that have at least one triple bond between two carbon atoms, with the formula CnH2n-2. The alkynes are traditionally known as acetylenes or the acetylene series, although the name acetylene is also used to refer specifically to the simplest member of the series, known as e...
.




uadricyclane is a highly toxic norbornadiene isomer
Isomer

In chemistry, isomers are compounds with the same molecular formula but different structural formulae. Isomers do not necessarily share similar properties unless they also have the same functional groups....
.






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Encyclopedia


Norbornadiene is a bicyclic hydrocarbon
Hydrocarbon

In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. With relation to chemical terminology, aromatic hydrocarbons or arenes, alkanes, alkenes and alkyne-based compounds composed entirely of carbon or hydrogen are referred to as "pure" hydrocarbons, whereas other hydrocarbons with bonded com...
. The molecule can be envisioned as a 1,4-cyclohexadiene bridged in the para positions by a methylene
Methylene

Methylene is the chemical species, R2C:, named after methane, in which two of the carbon atom's valence electrons form no bonds. The word is applicable to:...
 group. The compound is related to norbornene
Norbornene

Norbornene or norbornylene or norcamphene is a bridged cyclic hydrocarbon. It is a white solid with a pungent sour odor. The molecule consists of a cyclohexene ring bridged with a methylene group in the arene substitution patterns....
 in which one of the double bonds is saturated
Saturation (chemistry)

In chemistry, saturation has five different meanings:#In physical chemistry, saturation is the point at which a solution of a substance can dissolve no more of that substance and additional amounts of it will appear as a Precipitation ....
. Norbornadiene and related compounds are of great scientific interest because of the unusual geometry and high reactivity.

Synthesis

The norbornadiene framework is based on a Diels-Alder reaction
Diels-Alder reaction

The Diels-Alder reaction is an organic chemical reaction between a conjugated diene and a substituted alkene, commonly termed the dienophile, to form a substituted cyclohexene system....
 between a cyclopentadiene
Cyclopentadiene

Cyclopentadiene is a chemical compound with the Chemical formula C5H6. This colorless liquid organic chemistry chemical compound has a strong and unpleasant odor....
 and an alkyne
Alkyne

Alkynes are hydrocarbons that have at least one triple bond between two carbon atoms, with the formula CnH2n-2. The alkynes are traditionally known as acetylenes or the acetylene series, although the name acetylene is also used to refer specifically to the simplest member of the series, known as e...
.

Norbornadiene Synthesis



Reactions

Quadricyclane is a highly toxic norbornadiene isomer
Isomer

In chemistry, isomers are compounds with the same molecular formula but different structural formulae. Isomers do not necessarily share similar properties unless they also have the same functional groups....
. It can be obtained from norbornadiene by a photochemical reaction
Photochemical reaction

A photochemical reaction is a chemical reaction which is induced by electromagnetic wave . Examples of photochemical organic reactions are electrocyclic reactions, photoisomerization and Norrish reactions....
 when assisted by a sensitizer such as acetophenone
Acetophenone

Acetophenone is the organic compound with the chemical formula C6H5CCH3. It is the simplest aromatic ketone. This colourless, viscous liquid is a precursor to useful resins and fragrances....
. The norbornadiene-quadricyclane couple is of potential interest for solar energy storage when controlled release of the strain energy
Strain energy

In a molecule, strain energy is released when the constituent atoms are allowed to rearrange themselves in a chemical reaction or a change of chemical conformation in a way that:...
 stored in quadricyclane back to norbornadiene is made possible.

Quadricyclane



Quadricyclane is very reactive towards dienophiles in cycloaddition
Cycloaddition

A cycloaddition is a pericyclic chemical reaction, in which two pi bond are lost and two sigma bond are gained. The resulting reaction is a cyclization reaction....
 reactions. Norbornadienes also form organometallic complexes, where it can act as a two-electron or four-electron donor. Sandwich compounds such as tetracarbonyl(norbornadiene)chromium(0), which is a useful reagent for transferring chromium tetracarbonyl
Chromium carbonyl

Chromium carbonyl, also known as chromium hexacarbonyl, is the chemical compound with the chemical formula Cr6. At room temperature the solid is stable to air, although it does have a high vapor pressure and Sublimation s readily....
 to bidentate phosphine ligand
Ligand

In chemistry, a ligand is either an atom, ion, or molecule that bonds to a central metal, generally involving formal donation of one or more of its electrons....
s, are known.

Norbornadiene is also the starting material for the synthesis of diamantane and sumanene
Sumanene

Sumanene is a polycyclic aromatic hydrocarbon and of scientific interest because the molecule can be considered a fragment of buckminsterfullerene....
 and it is used as an acetylene
Acetylene

Acetylene is the chemical compound with the symbol carbonhydrogen. It is the simplest alkyne.As an alkyne, acetylene is Saturation because its two carbon atoms are Chemical bond together in a triple bond....
 transfer agent for instance in reaction with 3,6-di-2-pyridyl-1,2,4,5-tetrazine.

Further reading

  • Quadricyclane in Organic Syntheses
    Organic Syntheses

    Organic Syntheses is a scientific journal that since 1921 has provided the chemistry community with annual collections of detailed and checked procedures for the organic synthesis of organic compounds....
     Coll. Vol. 6, p.962; Vol. 51, p.133
  • Diamantane in Organic Syntheses
    Organic Syntheses

    Organic Syntheses is a scientific journal that since 1921 has provided the chemistry community with annual collections of detailed and checked procedures for the organic synthesis of organic compounds....
      Coll. Vol. 6, p.378; Vol. 53, p.30