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Regioselectivity in coupling reactions of α-naphthol
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Okesemilore Mary
Regioselectivity in coupling reactions of α-naphthol
The product at the para-position is more stable as it allows the compound to exist in the quinoid form, rather than only in the benzoid form:
This is important as in your case, if the substituent $\ce{X}$ is $\ce{H}$, then depending on the solvent, as much as 89% of it may exist in the quinoid form ($\bf{2}$).
References:
Satoshi Kishimoto, Shinya Kitahara, Osamu Manabe, Hachiro Hiyama, “Studies on coupling reactions of 1-naphthol. 6. Tautomerism and dissociation of 4-arylazo-1-naphthols in various solvents,” J. Org. Chem.1978, 43(20), 3882–3886 (https://doi.org/10.1021/jo00414a020).
The product at the para-position is more stable as it allows the compound to exist in the quinoid form, rather than only in the benzoid form:
This is important as in your case, if the substituent $\ce{X}$ is $\ce{H}$, then depending on the solvent, as much as 89% of it may exist in the quinoid form ($\bf{2}$).
References:
Satoshi Kishimoto, Shinya Kitahara, Osamu Manabe, Hachiro Hiyama, “Studies on coupling reactions of 1-naphthol. 6. Tautomerism and dissociation of 4-arylazo-1-naphthols in various solvents,” J. Org. Chem.1978, 43(20), 3882–3886 (https://doi.org/10.1021/jo00414a020).
The product at the para-position is more stable as it allows the compound to exist in the quinoid form, rather than only in the benzoid form:
This is important as in your case, if the substituent $\ce{X}$ is $\ce{H}$, then depending on the solvent, as much as 89% of it may exist in the quinoid form ($\bf{2}$).
References:
The product at the para-position is more stable as it allows the compound to exist in the quinoid form, rather than only in the benzoid form:
This is important as in your case, if the substituent $\ce{X}$ is $\ce{H}$, then depending on the solvent, as much as 89% of it may exist in the quinoid form ($\bf{2}$).
References:
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