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41.11.4.1 Synthesis of Product Subclass 4

DOI: 10.1055/sos-SD-041-00614

Collier, S. J.; Xiang, W.Science of Synthesis, (201041672.

N,N-Diiodoamines are highly unstable and are rarely reported in the literature. They have been prepared via the direct iodination of amines using iodine,[‌131‌,‌132‌] triiodoamineammonia complex,[‌133‌] N-iodosuccinimide,[‌132‌] or iodine monochloride (Scheme 19).[‌132‌] They have also been prepared through halogen metathesis of dibromoamines with iodine.[‌134‌] However, treatment of dichloroamines with potassium iodide gave a rapid reaction, but diiodoamine products could not be isolated.[‌118‌] Diiodoamines have been reported to form potentially polymeric complexes with other amines (or their precursors).[‌132‌,‌135‌] For example, treatment of methylamine with triiodoamineammonia polymeric complex [(NI3NH3)n] gives a polymeric complex of N,N-diiodomethylamine and methylamine [(MeNI2MeNH2)n].[‌135‌] Owing to the scarcity, instability, and difficult handling of diiodoamines, experimental procedures have not been provided.

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