76047-15-9

Upstream product

• 100-52-7 benzaldehyde 
• 76047-27-3 <1-(1-methylethoxy)-1-iodoethyl>triethylphosphonium iodide 
• 93-55-0 1-phenyl-propan-1-one 
• 67-63-0 isopropyl alcohol 
• 98990-64-8 4-Nitro-benzenesulfonic acid 1-methyl-2-oxo-2-phenyl-ethyl ester 

Relevant academic research and scientific papers

Sodium iodide-catalyzed direct α-alkoxylation of ketones with alcohols via oxidation of α-iodo ketone intermediates

The direct α-alkoxylation of ketones with alcohols via a sodium iodide-catalyzed oxidative cross-coupling has been developed. This protocol enables a range of alkyl aryl ketones to cross couple with an array of alcohols in synthetically useful yields. The mechanistic studies provided solid evidence supporting that an α-iodo ketone was a key reaction intermediate, being converted into an α-alkoxylated ketone via further oxidation to a hypervalent iodine species rather than a common nucleophilic substitution, and was generated from the ketone starting material via a radical intermediate. These new mechanism insights should have an effect on the design of iodide-catalyzed oxidative cross-coupling reactions between nucleophiles.

A facile synthesis of secondary α-alkoxy or α-acetoxy aromatic ketones

The treatment of HNIB with aromatic ketones and subsequent solvolysis using alcohol or acetic acid in one-pot system makes it possible to give corresponding secondary α-alkoxy or α-acetoxy ketones in high yields.

Chemistry of O-Alkyl Selenoesters. Reaction with Triethylphosphine

The reaction between triethylphosphine and a number of aliphatic and aromatic selenoesters under oxygen-free conditions have been investigated.The purple intermediate formed in the reaction with the aliphatic selenoesters was quenched with atmospheric oxygen and gave the corresponding esters, whereas quenching with methyl iodide gave the corresponding 1-alkoxy-1-iodoalkyltriethylphosphonium iodides (13)-(16).The 1-alkoxy-1-iodoalkyltriethylphosphonium iodides gave the 1-alkoxyalkyltriethylphosphonium iodides (17)-(20) upon treatment with methanol, and treatment with benzaldehyde at -70 deg C gave α-alkoxyalkyl phenyl ketones (22)-(25).The reaction between the selenobenzoates and triethylphosphine gave α-dialkoxy-stilbenes and -dibenzyls.When the reaction was carried out in cyclohexene 7-alkoxy-7-phenylbicycloheptanes were formed.The presence of benzaldehyde in the reaction mixture led to α-alkoxystilbenes.An explanation for these different reactions is presented.