It has been intensively studied owing to its high reactivity and distinctive structural property of being a diene that cannot isomerize (isomers would be anti-Bredt alkenes).
Norbornadiene can be formed by a Diels-Alder reaction between cyclopentadiene and acetylene[1] Quadricyclane, a valence isomer, can be obtained from norbornadiene by a photochemical reaction when assisted by a sensitizer such as acetophenone:[2] 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.
Norbornadiene is also the starting material for the synthesis of diamantane[4] and sumanene and it is used as an acetylene transfer agent for instance in reaction with 3,6-di-2-pyridyl-1,2,4,5-tetrazine.
[5] Norbornadiene is a versatile ligand in organometallic chemistry, where it serves as a two-electron or four-electron donor.
(Norbornadiene)molybdenum tetracarbonyl is used as a source of "Mo(CO)4", exploiting the lability of the diene ligand in this case.