75735-31-8

Upstream product

• 4846-21-3 O-phenylhydroxylamine 
• 100-52-7 benzaldehyde 
• 591-50-4 iodobenzene 
• 932-90-1 Benzaldoxime 
• 455-19-6 4-Trifluoromethylbenzaldehyde 
• 1948-40-9 4-hydroxy-3,5-diiodobenzaldehyde 
• 2973-77-5 3,5-dibromo-4-hydroxybenzaldehyde 
• 10203-08-4 3,5-dichlorobenzaldehyde 
• 447-61-0 2-Trifluoromethylbenzaldehyde 
• 619-21-6 m-formylphenyl benzoic acid 
• 454-89-7 3-Trifluoromethylbenzaldehyde 
• 99907-98-9 O-(3-(trifluoromethyl)phenyl)hydroxylamine 
• 32085-88-4 3,5-difluorobenzaldehyde 
• 83-38-5 2,6-dichlorobenzaldehyde 

Downstream Products

• 76570-67-7 Phenoxybenzamine 
• 100-47-0 benzonitrile 
• 3229-70-7 phenolate 
• 76570-73-5 N-Benzyl-N-phenoxy-benzamide 

Relevant academic research and scientific papers

Cul-mediated cross-coupling of aryl halides with oximes: A direct access to O-aryloximes

The first Cu-catalyzed cross-coupling of aromatic oximes and haloarenes is reported. This one-step formation of the =N-O-Ar linkage gives access to a range of oxime ethers in good to moderate yields.

Inhibitors of transthyretin amyloid fibril formation

Bisaryloxime ethers and bisarylhydroazones are shown to be effective for inhibiting formation of amyloid fibrils of transthyretin.

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.

Nitrile-forming Eliminations from Oxime Ethers

The oxime ethers (7) and (8) (R = alkyl or aryl) undergo base-catalysed elimination to benzonitriles (3) in water-dioxan (4 : 1) at 25 deg C.The Z-isomer (8Z) reacts via hydroxide-catalysed antiperiplanar elimination 70-fold more rapidly than the corresponding E-isomer.Electronic effects on syn-elimination (from 7E) show that electron-withdrawing groups aid elimination in both Ar and in the leaving group -OR; no intramolecular assistance is observed in these substrates.These results are interpreted in terms of a central E2 elimination, with appreciable C-H and N-O- bond cleavage in the transition state.