122969-82-8

Upstream product

• 55991-65-6 [1-(4-methoxyphenyl)vinyloxy]trimethylsilane 
• 75-07-0 acetaldehyde 
• 112481-61-5 C₁₈H₁₆F₃O₄Tl 
• 167367-46-6 1-(4-methoxyphenyl)butane-1,3-diol 
• 100-06-1 1-(4-methoxyphenyl)ethanone 

Downstream Products

• 97060-29-2 1-(4-methoxyphenyl)-but-2-en-1-one 
• 1408003-32-6 (Z)-6-acetoxy-4-methyl-6-(4-methoxyphenyl)-5-hexen-2-one 
• 122968-95-0 (E,3RS,1'RS)-3-(1'-hydroxy-1'-(4-methoxyphenyl)-2'-butenyl)-1-methyl-2-pyrrolidinone 
• 122968-96-1 (E,3RS,1'SR)-3-(1'-hydroxy-1'-(4-methoxyphenyl)-2'-butenyl)-1-methyl-2-pyrrolidinone 
• 97060-64-5 (E,2'RS,3'RS)- and (E,2'RS,3'SR)-1-(3'-hydroxy-3'-(4-methoxyphenyl)-2'-methyl-1'-oxo-4'-hexenyl)pyrrolidine 
• 97060-65-6 (2'RS,3'RS)- and (2'RS,3'SR)-1-(2',3'-dimethyl-5'-(4-methoxyphenyl)-1',5'-dioxopentyl)pyrrolidine 
• 122969-15-7 (3RS,1'RS)-3-(3'-(4-methoxyphenyl)-1'-methyl-3'-oxopropyl)-1-methyl-2-pyrrolidinone 
• 124781-41-5 1-(4-methoxyphenyl)-1,3-butanediol 

Relevant academic research and scientific papers

Visible light mediated chemo-selective oxidation of benzylic alcohols

A highly chemoselective visible light mediated strategy has been developed for oxidation of benzylic alcohols. The method circumvents the use of toxic metal catalysts, high energy light source, and operates at room temperature. Furthermore reaction is easily scalable to gram levels.

Osmium (VI) catalyzed chemoselective oxidation of allylic and benzylic alcohols

A mild and highly chemoselective approach to oxidation of allylic, electron rich/deficient benzylic, and heterocyclic alcohols employing catalytic quantities of K2[OsO2(OH)4] (3 mol %) and chloramine-T (50 mol %) is described. The protocol offers short reaction times (25 min-2 h), controlled oxidation, and tolerance to a variety of substrates. A systematic mechanistic study based on the LC-ESI-MS/MS reveals the presence of imidotriooxoosmium species which further reacts with alcohol to give the oxidized product.

InCl3/Me3SiCl-catalyzed direct michael addition of enol acetates to α,β-unsaturated ketones

The direct Michael addition of enol acetates to α,β-unsaturated ketones was achieved using a combination of Lewis acid catalysts, InCl 3 and Me3SiCl, which furnished stable enol-form products that could be further transformed into functionalized 1,5-diketones by reactions with various electrophiles.

Mpg-C3N4-catalyzed selective oxidation of alcohols using O2 and visible light

Mesoporous carbon nitride (mpg-C3N4) polymer can function as a metal-free photocatalyst to activate O2 for the selective oxidation of benzyl alcohols with visible light, avoiding the cost, toxicity, and purification problems associated with corresponding transition-metal systems. By combining the surface basicity and semiconductor functions of mpg-C3N4, the photocatalytic system can realize a high catalytic selectivity to generate benzaldehyde. The metal-free photocatalytic system also selectively converts other alcohol substrates to their corresponding aldehydes/ketones, demonstrating a potential pathway of accessing traditional mild radical chemistry with nitroxyl radicals.

Stereochemistry of the Michael Addition of N,N-Disubstituted Amide and Thioamide Enolates to α,β-Unsaturated Ketones

A systematic study of the regio- and diastereoselectivity of the kinetic Michael addition of amide and thioamide enolates to a series of α,β-unsaturated ketones has been carried out.Factors that influence the diastereo- and regiochemical outcome of the reaction include the substitution pattern of the enone and enolate, the enolate counterion, and the solvent.Numerous examples of high selectivity have been discovered.In a number of examples, either the syn or the anti addition products can be obtained by varying the nature of the solvent, donor atom, and/or counterion.These results have correlated in terms of a coherent transition-state model.

Metal-Metal Exchange of α-Metallo Ketones. Novel Formation of α-Acyl Anion and α-Keto Carbonium Ion Equivalents from (Aryl)phenacyl TlIII, PbIV, and HgII Systems

The novel class of α-metallo ketones RCOCH2TlIIItolyl(OCOCF3) where R = phenyl, substituted phenyl, thienyl, pyridinyl, and tert-butyl have been synthesized and characterized by 1H NMR and 13C NMR.These compounds serve as anion equivalents in the TiCl4-mediated aldol condensation.Metal-metal exchange with iodosylbenzene or lead tetraacetate leads to α-nucleophilic substitution derived from the formal α-keto carbonium ion equivalent.The corresponding p-CH3OC6H4COCH2PbIVC6H4OCH3-p-(OCOCH3)2 and (p-CH3OC6H4COCH2)2HgII analogues were synthesized and shown to likewise behave as either enolate anion or α-keto carbonium ion equivalents upon metal-metal exchange with TiIV, PbIV, or IIII.The importance of this work is that the range of reactivity of α-metallo ketones may be selectively adjusted by metal-metal or metal-metalloid exchange.