111750-22-2

Upstream product

• 98-95-3 nitrobenzene 
• 3282-30-2 pivaloyl chloride 
• 100-65-2 N-Phenylhydroxylamine 

Downstream Products

• 39837-50-8 N,N-diethyl-N'-phenyl-hydrazine 
• 1605281-59-1 tetrakis(hydroxamate) cerium(IV) 
• 74052-89-4 N-(4-hydroxyphenyl)-2,2-dimethylpropanamide 
• 371-40-4 4-fluoroaniline 
• 114995-47-0 N-(4-Fluorophenyl)-2,2-dimethylpropanamide 
• 446242-92-8 methyl (R)-(+)-1-phenylaziridine-2-carboxylate 
• 4916-14-7 methyl (S)-1-phenylaziridine-2-carboxylate 
• 37682-91-0 N-methyl-N,N′-diphenylhydrazine 
• 4916-14-7 methyl N-(phenyl)aziridine-2-carboxylate 

Relevant academic research and scientific papers

Redox-Neutral Selenium-Catalysed Isomerisation of para-Hydroxamic Acids into para-Aminophenols

A selenium-catalysed para-hydroxylation of N-aryl-hydroxamic acids is reported. Mechanistically, the reaction comprises an N?O bond cleavage and consecutive selenium-induced [2,3]-rearrangement to deliver para-hydroxyaniline derivatives. The mechanism is studied through both 18O-crossover experiments as well as quantum chemical calculations. This redox-neutral transformation provides an unconventional synthetic approach to para-aminophenols.

Structural and electrochemical characterization of a cerium(IV) hydroxamate complex: Implications for the beneficiation of light rare earth ores

Reaction of N-phenyl-pivalohydroxamic acid with CeIII precursors leads to a homoleptic hydroxamate complex: CeIV[tBuC(O) N(O)Ph]4. Electrochemical experiments indicate a significant stabilization of the CeIV cation at Ep,c = -1.20 V versus SCE in the hydroxamate ligand framework. The spontaneous oxidation of Ce III in a hydroxamate ligand field is discussed in the context of beneficiation of the light rare earths from the fluorocarbonate mineral bastn?site. the Partner Organisations 2014.

Asymmetric synthesis of N-aryl aziridines

The reactions of a variety of N-arylhydroxamates as nitrogen transfer reagents to acryloyl derivatives of (-)-8-phenylmenthol, (-)-quinine and (-)-Oppolzer's sultam acting as Michael acceptors was studied. Poor to modest diastereoselection was observed in the formation of aziridines. The absolute structure of one of the pure diastereomers secured from Oppolzer's auxiliary was established by X-ray crystallography and hence the absolute configuration of the derived methyl-N-phenylaziridine-2-carboxylate could be assigned. Whilst only poor facial selectivity was observed for chiral hydroxamic acid prepared from dehydroabietic acid, moderate to good enantioselection of aziridines could be achieved with the chiral quaternary salts based on cinchona alkaloids, especially with that of cinchonine. A model is presented to explain the origin of enantioselection and a mechanism is proposed for the aziridination reaction.