873998-30-2

Upstream product

• 938-87-4 2-methyl-1-phenyl-butan-1-one 
• 938-87-4 (+)-2-methyl-1-phenyl-butan-1-one 

Downstream Products

• 1342886-82-1 C₁₁H₁₅BrO 
• 68707-48-2 (E)-3-methyl-2-phenyl-pent-2-enenitrile 
• 68707-49-3 (Z)-3-methyl-2-phenyl-pent-2-enenitrile 
• 113598-56-4 2-benzyl-2-methyl-1-phenylbutan-1-one 
• 7505-96-6 2-hydroxy-2-methyl-1-phenylbutane-1-one 

Relevant academic research and scientific papers

Iron-Catalyzed Acyl Migration of Tertiary α-Azidyl Ketones: Synthetic Approach toward Enamides and Isoquinolones

This paper reports that tertiary α-azidyl phenyl ketones can be transformed into enamides by treatment with FeBr2 at elevated temperature in DMF. The reaction proceeds via 1,2-benzoyl migration from α-carbon to the nitrogen atom, accompanied by expulsion of a nitrogen molecule. This protocol is suitable for the synthesis of N-(cyclopent-1-en-1-yl)benzamides, N-(cyclohex-1-en-1-yl)benzamides, and N-benzoyl-α-methyl enamines and provides a convenient approach toward isoquinolones.

Intermolecular C-H Quaternary Alkylation of Aniline Derivatives Induced by Visible-Light Photoredox Catalysis

The intermolecular direct C-H alkylation of aniline derivatives with α-bromo ketones to build a quaternary carbon center was reported with a visible-light catalysis procedure. The reaction covers a variety of functional groups with good to excellent yield

Building Congested Ketone: Substituted Hantzsch Ester and Nitrile as Alkylation Reagents in Photoredox Catalysis

For the first time, 4-alkyl Hantzsch esters were used to construct molecules with all-carbon quaternary centers by visible light-induced photoredox catalysis via transfer alkylation. Up to a 1500 h-1 turnover frequency was achieved in this reaction. Reactions of 4-alkyl Hantzsch nitriles as tertiary radical donors joined two contiguous all-carbon quaternary centers intermolecularly, and this chemistry was used to synthesize a common precursor of a class of hydroxysteroid dehydrogenase inhibitors.

CF3CO2ZnEt-mediated highly regioselective rearrangement of bromohydrins to aldehydes

A highly efficient and selective rearrangement reaction of bromohydrins to aldehydes mediated by CF3CO2ZnEt was described. The secondary and tertiary aldehydes were prepared under mild conditions in good to excellent yields (85-99%). The scope and limitations of this rearrangement process were also investigated.

Enolisation baso-catalysee des cetones : 2e partie : Racemisation de methyl-2 phenyl-1 butanones-1 substituees en milieux fortement basiques

The base-catalyzed enolization of a ketone transforms the latter into an enolate ion via an activated complex in which a proton α to the carbonyl is transferred between its original site and the base catalyst.The position of the proton in the activated complex along the reaction pathway between the substrate and the base depends on the basic strengths of these entities.Some authors have suggested a regular variation of the position of the proton with the basicity of the medium, which led us to further investigate this question.We chose to use the Hammett correlation.As a matter of fact, Hammett's slope ρ correlates with the charge density on the substrate in the activated complex, therefore it was reasonable to think that the ρ values would be a function of the distance between the proton and the substrate.The experimental part of this work consists of the determination of enolization rates of substituted aromatic ketones in media of various basicities, in order to plot the correlation log10 k = (?).For practical reasons, we chose to study the racemization rates of five optically active substituted 2-methyl-1-phenyl-butan-1-ones.These ketones were synthesized by Friedel-Crafts reactions, which explains the fact that the substituents on the aromatic ring are essentially electrodonating : p-OCH3, 3',4'-dimethyl, p-CH3, H, p-Cl.The reaction media used are, by increasing basicities : water-dioxane 64/36 v/v + OH-, water-ethanol 1/2 + OH-/C2H5O-, ethanol + C2H5O-, ethanol-DMSO 2/1, 1/1 and 1/2 + C2H5O-, ethanol-HMPA 1/2 + C2H5O-.The ρ values in these solvents are respectively : 1.1, 2.0, 2.1, 2.2, 2.3, 2.4, 2.1.They are all positive.One finds that : 1. in strongly aqueous media, water-dioxane 64/36 and water (see preceding paper), ρ values are close to + 1, whereas in the other (slightly or non aqueous) media, they are of about + 2.This can be due to the nature of the base (OH- in one case and C2H5O- in the other), to the amount of water in the solvent, or to the nature of the organic solvent.One can also contemplate, as some authors did, the possibility of a change in the reaction mechanism according to the nature of the base. 2. if we take into account the experimental error on ρ values, there is only little (if any) change in the latter with the alkalinity of the medium (H functions for the various solvents used vary approximately from 14 to 19, which corresponds to an appreciable alkalinity increase).The conclusion is that the substrate retains the same charge density in the activated complex, the geometry of which consequently is the same in all media.According to the slope of the straight line log10 kobs = (H), which is 0.41 the proton being transferred in the activated complex could be slightly closer to the substrate than to the attacking base.