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It is employed in the aziridination of chiral N-enoyl sultams. It is also used in the synthesis of n-phthalimidoaziridines
Kung-Shou Yang.; Kwunmin Chen. Enantioselective aziridination of alkenes with N-aminophthalimide in the presence of lead tetraacetate-mediated chiral ligand.Org Lett.2002,4(7), 1107-1109.
David J. Anderson, et al. Reactive intermediates. Part XXII. Formation of 2H-azirines by oxidation of N-aminophthalimide in the presence of alkynes.J. Chem. Soc., Perkin Trans. 1.1973,550-555.
May be oxidized with lead(IV) acetate to "phthalimidonitrene", which adds to alkenes to give aziridines. The phthalimido group can be cleaved with hydrazine hydrate: J. Chem. Soc. (C), 576 (1970); J. Am. Chem. Soc., 92, 1784 (1970); Helv. Chim. Acta, 55, 1276 (1972); Org. Synth. Coll., 6, 56 (1988). Addition to cyclopentadienes leads to substituted pyridines after ring-opening with base: Heterocycles, 22, 1369 (1984). Addition to the (racemic) acrylic ester below shows an extremely high facial selectivity, adding to the less hindered side (290:1): Helv. Chim. Acta, 72, 1095 (1989).
Aziridination has also been achieved in high yield by electrochemical oxidation: J. Am. Chem. Soc., 124, 530 (2002).
Gefahrenhinweise (EU): H315-H319-H335
Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Do not breathe dust/fume/gas/mist/vapours/spray. Obtain special instructions before use. Wear protective gloves. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.