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Beilstein J. Org. Chem. 2011, 7, 1234–1248, doi:10.3762/bjoc.7.144
Graphical Abstract
Scheme 1: Proposed stepwise mechanism for the zincation of benzene.
Figure 1: Molecular structure of 2 with selective atom labelling. Hydrogen atoms and minor disorder component...
Scheme 2: Synergic metallation of N,N-dimethylaniline (A) with sodium TMP-zincate 1 to produce 2, which was s...
Figure 2: Molecular structure of 3 with selective atom labelling and thermal ellipsoids drawn at the 50% prob...
Scheme 3: Indirect zincation of N,N-dimethylaniline producing 4, 5 and 6, which was then quenched with I2 to ...
Figure 3: Molecular structure of 4 with selective atom labelling and thermal ellipsoids drawn at the 50% prob...
Figure 4: Solvent-separated ion-pair structure of 5 with selective atom labelling and thermal ellipsoids draw...
Figure 5: Molecular structure of 6 with selective atom labelling and thermal ellipsoids drawn at the 50% prob...
Figure 6: Aromatic region of 1H NMR spectra for deuterated benzene solutions of (a) the crude mixture obtaine...
Figure 7: Relative energy sequence of the four theoretical regioisomers of the experimentally observed produc...