90265-99-9

Upstream product

• 186581-53-3 diazomethane 
• 1929-29-9 3-(4-methoxyphenyl)propanoic acid 
• 15893-42-2 3-(4-methoxyphenyl)propionyl chloride 

Downstream Products

• 2472-22-2 6-methoxy-2-tetralone 

Relevant academic research and scientific papers

α-Xanthylmethyl Ketones from α-Diazo ketones

A simple and efficient method to obtain α-xanthylmethyl ketones from α-diazo ketones is described. The reaction proceeds through a protonation/nucleophilic substitution sequence in the presence of p -toluenesulfonic acid and potassium ethyl xanthogenate as the nucleophile. As α-diazo ketones can be readily synthesized from ubiquitous carboxylic acids, a broad variety of xanthates can be obtained, including examples from naturally occurring substrates.

The Intramolecular Buchner Reaction of Aryl Diazoketones. Substituent Effects and Scope in Synthesis

Rhodium(II) acetate-catalysed cyclisation of α-diazoketones derived from 3-arylpropionic acid produces bicyclodecatrienones or 2-tetralones depending on the substitution pattern of the aryl ring in the precursor; the former products are transformed into the latter catalytically with trifluoroacetic acid.Precursors with methyl, methoxy, and acetoxy substituents have been examined, efficient cyclisation occurring in all cases.When the precursor contains a meta-methoxy substituent, 2-tetralones are obtained directly.The efficient conversion of 3-phenylpropionicacid into trans-1-methylbicyclodecan-2-one is also described, partial asymmetric synthesis having been realised through the use of rhodium (S)-mandelate as the cyclisation catalyst.Cyclisations of diazoketones derived from 4-phenylbutyric acid and 5-phenylpentanoic acid have also been studied; the former provides a new entry into the bicycloundecane system whereas the latter produces a 2,3-disubstituted cyclopentanone via C-H insertion.Aspects of the cycloheptatriene-norcaradiene equilibrium in fused ring systems are discussed.

Efficient Synthesis of Bicyclodecatrienones and of 2-Tetralones via Rhodium(II) Acetate-catalysed Cyclisation of α-Diazoketones derived from 3-Arylpropionic Acids

Rhodium(II) acetate-catalysed cyclisation of α-diazoketones derived from 3-arylpropionic acids produces bicyclodecatrienones or 2-tetralones depending on the substitution pattern of the aryl ring; the former products are transformed into the latter by catalytic amounts of trifluoroacetic acid.

REGIOSPECIFIC SYNTHESIS OF α-(PHENYLTHIO)CYCLOALKENONES AND OF α-PHENYL-α-(PHENYLTHIO)KETONES VIA αα-ADDITION OF PHENYLSULPHENYL CHLORIDE TO α-DIAZOKETONES

Cyclic α-diazoketones react with phenylsulphenyl chloride at room temperature to furnish α-chloro-α-(phenylthio)cycloalkanones which undergo ready dehydrochlorination to α-(phenylthio)cycloalkenones when treated with triethylamine; acyclic, terminal α-diazoketones also furnish α-chloro-α-(phenylthio)adducts which are useful electrophiles in the synthesis of α-phenyl-α-(phenylthio)ketones.