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1 article(s) from Balloch, Liam

Meta-metallation of N,N-dimethylaniline: Contrasting direct sodium-mediated zincation with indirect sodiation-dialkylzinc co-complexation

David R. Armstrong,
Liam Balloch,
Eva Hevia,
Alan R. Kennedy,
Robert E. Mulvey,
Charles T. O'Hara and
Stuart D. Robertson

Beilstein J. Org. Chem. 2011, 7, 1234–1248, doi:10.3762/bjoc.7.144

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Scheme 1: Proposed stepwise mechanism for the zincation of benzene.

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Figure 1: Molecular structure of 2 with selective atom labelling. Hydrogen atoms and minor disorder component...

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Scheme 2: Synergic metallation of N,N-dimethylaniline (A) with sodium TMP-zincate 1 to produce 2, which was s...

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Figure 2: Molecular structure of 3 with selective atom labelling and thermal ellipsoids drawn at the 50% prob...

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Scheme 3: Indirect zincation of N,N-dimethylaniline producing 4, 5 and 6, which was then quenched with I₂ to ...

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Figure 3: Molecular structure of 4 with selective atom labelling and thermal ellipsoids drawn at the 50% prob...

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Figure 4: Solvent-separated ion-pair structure of 5 with selective atom labelling and thermal ellipsoids draw...

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Figure 5: Molecular structure of 6 with selective atom labelling and thermal ellipsoids drawn at the 50% prob...

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Figure 6: Aromatic region of ¹H NMR spectra for deuterated benzene solutions of (a) the crude mixture obtaine...

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Figure 7: Relative energy sequence of the four theoretical regioisomers of the experimentally observed produc...

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Published 06 Sep 2011

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