69373-32-6

Upstream product

• 110-22-5 diacetyl peroxide 
• 103-79-7 1-phenyl-acetone 
• 66217-87-6 (E)-N-(1-methyl-2-phenethenyl)morpholine 
• 705-60-2 (2-nitroprop-1-enyl)benzene 
• 18649-43-9 4-methoxyphenyllead(IV) triacetate 
• 57918-71-5 1-Phenyl-2-propanone Potassium Enolate 
• 42124-16-3 1,5-diphenyl-2,4-dimethyl-1,4-pentadien-3-one 

Downstream Products

• 96585-35-2 N-phenyl-2,5-dimethyl-3,4-diphenylpyrrole 
• 79823-43-1 1-benzyl-3,4,-diphenyl-2,5-dimethylpyrrole 

Relevant academic research and scientific papers

1,4-Diketones from Cross-Conjugated Dienones: Potassium Permanganate-Interrupted Nazarov Reaction

A domino potassium permanganate-interrupted Nazarov reaction to yield syn-2,3-disubstituted 1,4-diketones via a decarbonylative cleavage of the Nazarov oxyallyl intermediate, believed to be without precedent, is presented. This process allows syn substituents to be established stereospecifically on the 2-carbon bridge connecting the ketone carbonyl carbons, and the formation of one carbon-carbon and two carbon-oxygen bonds. Two carbon-carbon bonds are cleaved in this process.

α-Arylation of ketones by aryllead triacetates. Effect of methyl and phenyl substitution at the α position

An examination of the α-arylation of a number of ketones and their enolate salts by p-methoxyphenyllead triacetate provides further evidence for a very marked selectivity in the arylation reaction. It is found that the reaction proceeds well at tertiary α-carbons and at secondary centres activated by the presence of a phenyl group, but fails where the secondary centre is unactivated and at primary α-carbons.

CARBO- AND HETEROCYCLIZATION REACTIONS OF 2-(4-MORPHOLINYL)-1-PHENYLPROPENE AND NITROOLEFINS

The title enamine may exist in two double bond isomers.Both forms react with the nitroolefins under different conditions to afford, after hydrolysis, regioisomeric γ-nitroketones. γ-Dicarbonyl compounds are isolated from the hydrolysis at pH 2 of the 1,2-oxazine N-oxide systems, which in some cases have also been separated.

Stereoisomer Effects on the Paal-Knorr Synthesis of Pyrroles

The neurotoxicity of n-hexane has been postulated to result from the reactivity of its γ-diketone metabolite, 2,5-hexanedione (1), with lysil amino groups of proteins to form pyrroles (Paal-Knorr synthesis).We have synthesized a series of 3,4-disubstituted γ-diketones in order to explore the relationship between rate of pyrrole formation and neurotoxicity.The γ-diketones were prepared through oxidative coupling of ketones.Yields were improved to 60-70percent with the use a Soxhlet apparatus containing PbO2 in the extraction thimble.Diketones prepared were 3,4-dimethylhexane-2,5-dione (2), 3,4-diethylhexane-2,5-dione (3), 3,4-diisopropylhexane-2,5-dione (4), and 3,4-diphenylhexane-2,5-dione (5).The reactions yielded mixtures of the d,l (a) and meso (b) diastereomers, which were separated by column chromatography, fractional distillation, or crystallization.Structures of the diastereomeric forms were established by 13C NMR techniques and, in the case of 4b, by single crystal X-ray diffraction.The relative reactivities of the d,l and meso isomers of each γ-diketone were determined with benzylamine in cyclohexane and the rate of pyrrole formation was determined by HPLC.For each pair of diastereomeric diketones the d,l reacted 4-40 times faster than the meso form.The reactivities of the γ-diketones were in the order 2 > 1 > 3 > 5 > 4 with pseudo-first-order rate constants ranging from 4*10-4 to 3*10-8 s-1 at 30 deg C.