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January 1, 1979Journal of the Chemical Society Perkin Transactions 2

Catalysis in aromatic nucleophilic substitution. Part 4. Reactions of piperidine with 2-methoxy-3-nitrothiophen in benzene

Giovanni Consiglio Renato Noto Domenico Spinelli

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Abstract

The rate of piperidino-substitution of 2-methoxy-3-nitrothiophen (I) in benzene as a function of amine concentration has been studied. The reaction is strongly catalysed by piperidine, being third-order overall (second-order in amine) and represents the first example of an SNAr of an ortho- or ortho-like mononitro-substituted derivative for which base catalysis is needed in benzene. The results obtained have been interpreted by taking into account the properties of the leaving group and its peculiar ortho-like relation with the activating nitro group.

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Consiglio et al. (1979) studied this question.

synapsesocial.com/papers/6a923d6952abdb5175435f04 https://doi.org/10.1039/p29790000222

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