Arylacetic acid esters

Br a-Hydroxy-arylacetic acid esters were oxidized with bromide ion as a mediator to give a-oxo-arylacetic acid esters [37]. 

Reaction of aldehydes with ethyl diazoacetate normally results in the formation of [5-oxo esters. When a cationic Fe(II) Lewis acid is used as the catalyst, an unexpected 1,2-aryl shift results in the formation of a-formyl arylacetic acid ester 23, which is isolated as its enol tautomer (Scheme 8.6) [28]. The catalyst of this reaction,... 

Matsumura and his coworkers [38] have employed the 2-pyrrolidone anion, in DMF solution, to deprotonate arylacetic acid esters with subsequent oxidative dimerization of the corresponding carbanions. This study includes a useful comparison between the electrochemical and chemical generation of the 2-pyrrolidone anion (by fluoride anion displacement in A-trimethylsilyl-2-pyrrolidone). The advantage lies with the electrochemical route, which gave yields of final product of 80%, compared with the 30% obtained with the chemically generated base (Scheme 10). The overall process, formation of dimethyl 2,3-diphenylsuccinates, is not only efficient and convenient but also operates with high diastereoselectivity when under the control of an oxazolidinone chiral auxiliary (Scheme 10). 

Arylacetic acid esters from acylophenones 1,2-Aryl migration under mild conditions... 

Thallic nitrate s. under HCIO4 Perchloric acid/thallic nitrate Arylacetic acid esters... 

Thallic nitrate perchloric acid Arylacetic acid esters from aryl methyl ketones... 

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