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2,5-Norbornadiene is used as an intermediate in prostaglandin synthesis and shows anti-ethylene effect on plants. It acts as a starting material for the synthesis of diamantane and as an acetylene transfer agent for instance, in reaction with 3,6-di-2-pyridyl-1,2,4,5-tetrazine. It is also a useful dienophile in Diels-Alder reactions.
Bidentate π -ligand.
The 2,4-pentanedionatorhodium complex: J. Chem. Soc. (A), 2334 (1971) has been used in the preparation of a chiral BINAP catalyst for homogeneous asymmetric hydrogenation: Org. Synth. Coll., 8, 420 (1993); see also (R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl, B23785.
Cycloaddition with Tetraphenylcyclopentadienone, A12756, is followed by retro-Diels-Alder reaction with loss of cyclopentadiene to give 1,2,3,4-tetraphenylbenzene: J. Chem. Soc., 473 (1960).
Similarly, pyrolysis of the adduct formed by 1,3-dipolar cycloaddition of acrylonitrile oxide provides a high-yield route to 3-vinylisoxazole: J. Chem. Soc., Chem. Commun., 2661 (1994)./n
Aida, F.; Sone, H.; Ogawa, R.; Hamaoka, T.; Shimizu, I. Palladium-catalyzed 5-exo-Selective Reductive Mizoroki-Heck Reaction of Aryl Chlorides with 2,5-Norbornadiene. Chem. Lett.2015,44 (5), 715-717.
Jia, H.; Shi, Y.; Ma, L.; Wang, Y.; Zang, Y.; Peng, J. Asymmetric polymerisation of substituted phenylacetylene using chiral Rh(2,5-norbornadiene)(L-proline) catalyst. Chem. Pap. 2015, 69 (5), 756-760.
Hazard Statements: H225-H303
Highly flammable liquid and vapour. May be harmful if swallowed.
Precautionary Statements: P210-P280a-P240-P241-P303+P361+P353-P501a
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Wear protective gloves and eye/face protection. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. Dispose of contents/container in accordance with local/regional/national/international regulations.