76570-51-9

Upstream product

• 6092-74-6 N-benzoyloxycarbonylphenylhydroxylamine 
• 77-78-1 dimethyl sulfate 
• 121989-74-0 O-benzyl-N-methoxycarbamate 
• 71-43-2 benzene 
• 501-53-1 benzyl chloroformate 
• 1483-73-4 diphenyliodonium bromide 
• 3426-71-9 Benzyl N-hydroxycarbamate 
• 121989-76-2 C₉H₁₀ClNO₃ 

Relevant academic research and scientific papers

An Improved Catalyst for Iodine(I/III)-Catalysed Intermolecular C H Amination

1,2-Diiodobenzene is presented as an efficient catalyst precursor for the intermolecular amination of arenes under homogeneous conditions. N-Troc- and N-phthalimido-substituted methoxyamines serve as suitable nitrogen sources providing the corresponding aniline derivatives in up to 99% yield and with up to 66:1 regioselectivity. Key for this successful C N coupling protocol is the strained μ-oxo-bridged conformation of the bisiodine(III) catalyst, which induces unparalleled high reactivity. (Figure presented.) .

Cesium Carbonate Promoted Direct Arylation of Hydroxylamines and Oximes with Diaryliodonium Salts

A transition-metal-free approach for the arylation of hydroxylamines and oximes with diaryliodonium salts was developed. The reaction proceeded smoothly at room temperature in the presence of cesium carbonate. As a result, a wide range of N- and O-arylate

An Electrophilic Aromatic Substitution by N-Methoxyamides via Hypervalen Iodine Intermediates

Treatment of N-methoxyamides with hypervalent iodine compounds generates electron deficient nitrogen species which react intra- or intermolecularly with an aromatic group to give N-aryl-N-methoxyamides in good yields.

Electrophilic Aromatic Substitution with N-Methoxy-N-acylnitrenium Ions Generated from N-Chloro-N-methoxyamides: Syntheses of Nitrogen Heterocyclic Compounds Bearing a N-Methoxyamide Group

N-Methoxy-N-acylnitrenium ions (II), generated by treatment of N-chloro-N-methoxyamides with silver carbonate in trifluoroacetic acid, react with arenes to give N-aryl-N-methoxyamides in good yields.In the case of the intramolecular cyclization of N-chloro-N-methoxy-2-phenylacetamides, the mode of cyclization is highly dependent on the nature of ortho or para substituent groups.Nitrenium ions II can primarily attack three positions (C-1, C-2, and C-6) of a phenyl ring.Normally II attack C-6.On the other hand, when the ortho position was occupied with a substituent group, II attacked both C-2 and C-6, in the former case followed by a 1,2-substituent migration, which was proved by a deuterium labeling experiment.Especially, when a methoxy group is substituted on ortho or para position, II attack C-1 due to the effect of the electron-releasing methoxy group to give spiro dienone compounds 39.A general discussion of the utility and mechanistic details of these reactions is presented.

Studies on the Preparation of N-Alkyl-O-phenylhydroxylamines

Several possible routes to the title compounds have been investigated.The reaction of N-hydroxycarbamates (1) with diphenyliodonium bromide gave, unexpectedly, N-hydroxy-N-phenylcarbamates (2), while N-methyl-N-hydroxycarbamates (6) gave 2-(N-methyl-N-alkoxycarbonylamino)phenols (7).Mechanistic aspects of the N-arylations and subsequent rearrangements are discussed.The desired N-alkyl-O-phenylhydroxylamines were obtained by the reduction of O-phenyloximes (15) with sodium cyanoborohydride.