1079437-81-2

Upstream product

• 1101835-32-8 2,2-dimethyl-1-phenylpent-4-en-1-one dioxime oxalate 
• 71-43-2 benzene 
• 1583276-54-3 (Z)-2,2-dimethyl-1-phenylpent-4-en-1-one oxime 
• 611-70-1 phenyl isopropyl ketone 
• 39576-24-4 2,2-dimethyl-1-phenyl-4-pentene 
• 852058-12-9 1-phenyl-2,2-dimethylpent-4-en-1-one oxime 

Relevant academic research and scientific papers

Iron-Catalyzed Aminative Cyclization/Intermolecular Homolytic Aromatic Substitution Using Oxime Esters and Simple Arenes

Intermolecular C?H alkylation of simple arenes in the presence of an iron catalyst has been achieved in a cascade manner with an aminative cyclization triggered by N?O bond cleavage of an alkene-tethered oxime ester. Various arenes, including electron-rich and electron-poor arenes, and heteroarenes can be employed in the reaction system. Regioselectivity and radical trapping experiments support the involvement of alkyl radical species, which undergo a homolytic aromatic substitution (HAS) to afford the arylation products.

Pyrroline Synthesis via Visible-Light-Promoted Hydroimination of Unactivated Alkenes with N,N′-Dimethylpropylene Urea as H-Donor

Synthesis of 3,4-pyrroline derivatives via visible-light-induced hydro/oxyimination of unactivated olefins is reported. In the presence of the photoredox catalyst fac-Ir(ppy)3, the key iminyl radical intermediate can be readily generated from O-acyl oximes, and undergoes intramolecular cyclization and H-abstraction from solvent or is trapped by TEMPO to give the corresponding hydro/oxyimination product, respectively. Mechanistic investigations indicate that N,N′-dimethylpropylene urea (DMPU) works as both reducing agent for catalyst regeneration and H-donor for product formation in this process. (Figure presented.).

Visible-Light-Mediated Iminyl Radical Generation from Benzyl Oxime Ether: Synthesis of Pyrroline via Hydroimination Cyclization

The treatment of an O-(4-methoxybenzyl) oxime ether bearing an olefin substituent and 1-chloroanthraquinone (1-Cl-AQN) catalyst in 2-butanone under visible-light irradiation affords pyrroline via an iminyl radical intramolecular hydroimination. Mechanistic studies indicate that iminyl radical generation mainly proceeds by hydrogen abstraction of the photocatalyst from the benzyl position of the oxime. Moreover, the hydrogen atom was identified in circulation from the benzylic position of the substrates between AQN and 2-butanone to quench the carbon radical without requiring any additional reagents.

Dioxime oxalates; new iminyl radical precursors for syntheses of N-heterocycles

Symmetrical and unsymmetrical dioxime oxalates were prepared by treatment of oximes with oxalyl chloride. UV photolysis of these precursors was found to be an atom-efficient way of generating iminyl radicals. The process was most efficient for dioxime oxalates having aryl substituents attached to their C{double bond, long}N bonds. The method was useful for EPR spectroscopic study of iminyl and iminoxyl radicals. Photolyses in toluene solution, of dioxime oxalates containing alkenyl acceptor groups, yielded unsaturated iminyl radicals that ring closed to afford 3,4-dihydro-2H-pyrroles in good yields. Dioxime oxalates with biphenyl substituents also released iminyl radicals that ring closed onto the aromatic acceptor groups and, in acetonitrile solution, this approach provided a useful and atom-efficient method of making substituted phenanthridines.

From dioxime oxalates to dihydropyrroles and phenanthridines via iminyl radicals

Dioxime oxalates are useful precursors for the clean generation of iminyl radicals by sensitised UV photolysis and can be adapted for serviceable preparations of 3,4-dihydro-2H-pyrroles and phenanthridines. The Royal Society of Chemistry.