Abstract
The reactions of n-butylamine, pyrrolidine and piperidine with phenyl 2,4,6-trinitrophenyl ether, 3, in DMSO result in the rapid reversible formation of adducts by reaction at the 3-position followed by attack at the 1-position leading to substitution of the phenoxy group. With phenyl 2,4-dinitronaphthyl ether, 1a, and phenyl 2,4-dinitrophenyl ether, 8, substitution is the only process observed. For each substrate reactions with n-butylamine show a first order dependence on the amine concentration indicating that nucleophilic attack is rate-limiting. However, the reactions with pyrrolidine and with piperidine are subject to general base catalysis and it is argued that here the deprotonation of the initially formed zwitterionic intermediates is rate determining. The results are compared and contrasted with those of the corresponding ethyl ethers, where base catalysis involves the SB-GA mechanism, and with phenyl sulfides.
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
More From: Journal of the Chemical Society, Perkin Transactions 2
Disclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.