Everything about Norbornadiene totally explained
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Norbornadiene is a bicyclic
hydrocarbon. The molecule can be envisioned as a 1,4-cyclohexadiene bridged in the
para positions by a
methylene group. The compound is related to
norbornene in which one of the
double bonds is
saturated. 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 between a
cyclopentadiene and an
alkyne.
»
Reactions
Quadricyclane is a highly toxic
4 norbornadiene
isomer. It can be obtained from norbornadiene by a
photochemical reaction when assisted by a
sensitizer such as
acetophenone. The norbornadiene quadricyclane couple is of potential interest for
solar energy storage when controlled release of the
strain energy stored in quadricyclane back to norbornadiene is made possible.
1 Quadricyclane is very reactive towards
dienophiles in
cycloaddition reactions.
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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),
3 which is a useful reagent for transferring
chromium tetracarbonyl to
bidentate phosphine
ligands, are known.
Norbornadiene is also the starting material for the synthesis of
diamantane and
sumanene and it's used as an
acetylene transfer agent for instance in reaction with
3,6-di-2-pyridyl-1,2,4,5-tetrazine.
2Further Information
Get more info on 'Norbornadiene'.
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