A Lewis acid catalyzed 1, 2 aryl shift in. alpha.-haloalkyl aryl acetals: a convenient route to. alpha.-arylalkanoic acids

…, A Belli, F Uggeri, C Giordano

Index: Castaldi, Graziano; Belli, Aldo; Uggeri, Fulvio; Giordano, Claudio Journal of Organic Chemistry, 1983 , vol. 48, # 24 p. 4658 - 4661

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Citation Number: 28

Abstract

A new method for the synthesis of a-arylalkanoic acids is given, based on Lewis acid promoted rearrangement of acetals of primary and secondary a-haloalkyl aryl ketones (halo= Br, C1) in hydrocarbon solvents. The reaction is selective, providing the esters of a- arylalkanoic acids in almost quantitative yields. The ability of “soft and borderline” Lewis acids in activating the carbon-halogen bond is compared with that of silver salts. The ...

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