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5-Norbornene-2-carboxaldehyde was used in transition metal-catalyzed synthesis of norbornene-derived homopolymers having pendent t-Boc-protected quinizarin moieties for patterned fluorescence images. It acts as Diels-Alder adduct of acrolein and cyclopentadiene. It can be used as protected form of acrolein, from which the double bond may be liberated by cycloreversion, e.g. in a useful synthesis of 2-vinylimidazole.
Jimmy Yoo; Jae-Hyoung Lee; Iwhan Cho; Kwang-Duk Ahn; Jong-Man Kim. The first synthesis of a transition metal-catalyzed homopolymer having pendentt-boc-protected quinizarin for patterned fluorescence images. Macromolecular Research.2003, 11, 69-72.
Diels-Alder adduct of acrolein and cyclopentadiene. Can be used as protected form of acrolein, from which the double bond may be liberated by cycloreversion, e.g. in a useful synthesis of 2-vinylimidazole: Angew. Chem. Int. Ed., 22, 560 (1983):
Aldol condensation with formaldehyde, followed by crossed Cannizzaro reduction, gives norbornene-2,2-dimethanol, from can be thermolyzed to vinyl-1,1-dimethanol: Tetrahedron Lett., 3775 (1975). For a review of cycloreversion reactions in organic synthesis, see: Synthesis, 121 (1985).
Hazard Statements: H226
Flammable liquid and vapour.
Precautionary Statements: P210-P233-P240-P241-P242-P243-P280-P303+P361+P353-P374-P380-P501c
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep container tightly closed. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Use only non-sparking tools. Take precautionary measures against static discharge. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. Fight fire with normal precautions from a reasonable distance. Evacuate area. Dispose of contents/ container to an approved waste disposal plant