Conclusions
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1.
The acid-catalyzed Claisen rearrangement in a series of N-allylanilines in nitrobenzene is always accompanied by the elimination reaction, but its contribution to the total process is different, depending on the allyl substituent. On the basis of an analysis of the activation parameters, it is judged that the reactions proceed through an ion-pair mechanism.
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2.
A molar excess of the substrate in comparison with the catalyst has identical inhibiting effects on the rearrangement and elimination, owing to the formation of a nonreactive complex with the composition [amine]∶[HCl]=2∶1.
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Translated from Izvestiya Akademii Nauk SSSR, Seriva Khimicheskaya, No. 6, pp. 1273–1277, June, 1983.
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Abdrakhmanov, I.B., Sharafutdinov, V.M., Nigmatullin, N.G. et al. Claisen rearrangement in N-allylaniline series. Russ Chem Bull 32, 1149–1153 (1983). https://doi.org/10.1007/BF00953146
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DOI: https://doi.org/10.1007/BF00953146