Substituted benzamides have been widely employed as valuable synthons for metalation reactions encompassing a wide variety of applications. Recently, research has lead to interest in dihalogenated benzamides for use as pest control agents. Previous studies of this laboratory group have revealed that metalation reactions with secondary 3,5-dichloro-substituted benzamides afford products resulting from ortho-metalation while metalation reactions with the corresponding tertiary dichloro-substituted benzamides afford only products resulting from para-metalation. To better understand the influence of halogens on the regioselectivity of these reactions, the corresponding 3,5-difluoro-substituted analogs were studied. Metalation studies with N-ethyl-3,5-difluorobenzamide indicate that products arising from both para- and ortho-metalation were produced, while initial results from the metalation of N,N-diethyl-3,5-difluorobenzamide indicate that products resulting from para-metalation were favored.
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Back to The 37th Middle Atlantic Regional Meeting (May 22-25, 2005)