An article PIFA-Promoted, Solvent-Controlled Selective Functionalization of C(sp(2))-H or C(sp(3))-H: Nitration via C-N Bond Cleavage of CH3NO2, Cyanation, or Oxygenation in Water WOS:000467320000028 published article about HYPERVALENT IODINE REAGENTS; AROMATIC NITRATION; TERTIARY-AMINES; H FUNCTIONALIZATION; CONJUGATE ADDITION; SODIUM-NITRITE; UREA NITRATE; NITROMETHANE; OXIDATION; ATOM in [Kim, Mi-hyun] Gachon Univ, Coll Pharm, Gachon Inst Pharmaceut Sci, 191 Hambakmoeiro, Incheon 21936, South Korea; Gachon Univ, Coll Pharm, Dept Pharm, 191 Hambakmoeiro, Incheon 21936, South Korea in 2019, Cited 71. Recommanded Product: 1,4-Dioxa-8-azaspiro[4.5]decane. The Name is 1,4-Dioxa-8-azaspiro[4.5]decane. Through research, I have a further understanding and discovery of 177-11-7
A novel nitration (via C(sp(3))-N breaking/C(sp(2))-N formation with CH3NO2) mediated by [bis-(trifluoroacetoxy)iodo]benzene (PIFA) is described. The NO2 transfer from CH3NO2 to the aromatic group of the substrate is possible with careful selection of the solvent, NaX, and oxidant. In addition, the solvent-controlled C(sp(2))-H functionalization can shift to an alpha-C(sp(3))-H functionalization (cyanation or oxygenation) of the alpha-C(sp(3))-H of cyclic amines.
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Reference:
Piperidine – Wikipedia,
Piperidine | C5H7510N – PubChem