Base Catalysis in Nucleophilic Aromatic Substitution Reactions: Evidence for Cyclic Transition State Mechanism over the Dimer Mechanism in a Non-polar Aprotic Solvent
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Source and publish data:
Journal of the Chemical Society. Perkin transactions II p. 531 - 536 (1986)
Update date:2022-08-18
Topics:
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Authors:
Banjoko, Olayinka
Ezeani, Chike
Article abstract of DOI:10.1039/P29860000531
The reactions of X-phenyl 2,4,6-trinitrophenyl ethers with aniline in benzene display three distinct mechanisms even though all except the 2,6-dinitrophenyl ether are base catalysed.The catalysis of the mononitro-substituted ethers involves two aniline molecules and proceeds at a temperature-independent rate in the temperature range 5 - 35 deg C while that of the dinitro-substituted ones involves only one aniline molecule and proceeds at a temperature-dependent rate over the same temperature range.The results are interpreted in terms of a cyclic mechanism involving four-, six-, and eight-membered rings in the transition state.
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Full text of DOI:10.1039/P29860000531
