Nucleophilic addition of silyl enol ethers to aromatic nitro compounds: scope and mechanism of reaction

TV RajanBabu, GS Reddy…

Index: RajanBabu, T. V.; Reddy, G. S.; Fukunaga, Tadamichi Journal of the American Chemical Society, 1985 , vol. 107, # 19 p. 5473 - 5483

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Citation Number: 74

Abstract

Abstract: In sharp contrast to alkali-metal enolates, silyl enol ethers and ketene silyl acetals add to aromatic nitro compounds in the presence of a fluoride ion source to give the intermediate dihydroaromatic nitronates, which can be observed by NMR. In situ oxidation of the intermediate with bormine or DDQ yields a-nitroaryl carbonyl compounds in moderate-to- high yields. The reaction is applicable to alkyl-, alkoxy-, and halogen-substituted ...

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