Meta-Metallation of N,N-Dimethylaniline
Author Information
Author(s): David R. Armstrong, Liam Balloch, Eva Hevia, Alan R. Kennedy, Robert E. Mulvey, Charles T. O'Hara, Stuart D. Robertson, Victor Snieckus
Primary Institution: University of Strathclyde
Hypothesis
Can sodium-mediated zincation lead to meta-metallation of N,N-dimethylaniline?
Conclusion
The study demonstrates that sodium-mediated zincation can selectively produce the meta-isomer of N,N-dimethylaniline.
Supporting Evidence
- The reaction of N,N-dimethylaniline with sodium TMP-zincate produced a mixture of ortho-, meta-, and para-regioisomers.
- The meta-isomer was isolated in reasonable yields in a clean, pure crystalline form.
- DFT calculations supported the experimental findings, indicating that the meta-isomer is the energetically preferred product.
Takeaway
This research shows how a special chemical reaction can change where a metal attaches to a molecule, making it possible to create new types of compounds.
Methodology
The study involved synthesizing and characterizing various organometallic complexes through reactions of N,N-dimethylaniline with sodium TMP-zincate and other reagents, followed by NMR and X-ray crystallography analysis.
Limitations
The study may be limited by the stability of the intermediates and the conditions required for the reactions.
Digital Object Identifier (DOI)
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