Zhang, Guangyu published the artcileDiverse and chemoselective sigmatropic shift rearrangements of multisubstituted N,O-diarylhydroxylamines, COA of Formula: C7H3IN2O2, the publication is Organic & Biomolecular Chemistry (2022), 20(27), 5470-5480, database is CAplus and MEDLINE.
Possible N/O[1,3] sigmatropic shift rearrangements of multisubstituted N,O-diarylhydroxylamines were investigated exptl. with rationally designed substrates, which were generally in situ prepared from suitable nitroaryl halides and N-arylhydroxylamines via aromatic nucleophilic substitution. The results indicate that both N- and O-(2,4,6-trimethylphenyl)hydroxylamines still favor the [3,3] sigmatropic shift followed by tautomerization rather than N[1,3] and O[1,3] sigmatropic shifts and the rearranged products of N-(2,4,6-trimethylphenyl)hydroxylamines further undergo an intramol. nucleophilic addition to afford dibenzo[b,d]furan-4a(9bH)-amine derivatives I [R = H, NO2; EWG = NO2, CN], while N-(4-mono- and 3,5-disubstituted phenyl)-O-(2,4,6-trinitrophenyl)hydroxylamines favorably first undergo the O[1,3] sigmatropic shift followed by tandem Smiles rearrangement and amide/ester exchange reactions, generating 2-arylaminoaryl benzoate derivatives N-Phenyl-O-(2,4,6-trinitrophenyl)hydroxylamines undergo tandem double O[1,3] sigmatropic shift rearrangement to produce formal O[1,5] shift products. However, O-(2,6-dinitrophenyl)-N-(4-substituted phenyl)hydroxylamines undergo tandem O[1,3] and double [3,3] sigmatropic shift rearrangements to give formal 3,5-shift products. The proposed mechanism was rationalized by d. functional theory (DFT) calculations The current investigation provided not only a comprehensive understanding of the chemoselective sigmatropic shift rearrangements of N,O-diarylhydroxylamines, but also some novel synthetic strategies for dibenzo[b,d]furanamines, diarylamines, diaryl ethers, 2′-amino-[1,1′-biphenyl]-2(1H)-one, and 2′-amino-[1,1′-biaryl]-4-ol derivatives
Organic & Biomolecular Chemistry published new progress about 101420-79-5. 101420-79-5 belongs to iodides-buliding-blocks, auxiliary class Nitrile,Nitro Compound,Iodide,Benzene,Benzene Compounds, name is 4-Iodo-3-nitrobenzonitrile, and the molecular formula is C10H10O2, COA of Formula: C7H3IN2O2.
Referemce:
https://en.wikipedia.org/wiki/Iodide,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com