Über die Sandmeyersche Reaktion I Die Bildung von Phenolen und Halogenbenzolen bei der Zersetzung der Diazoniumhalogenide

doi:10.1002/jlac.19495610308

Justus Liebigs Ann. Chem.

1949

DOI: 10.1002/jlac.19495610308

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Über die Sandmeyersche Reaktion I Die Bildung von Phenolen und Halogenbenzolen bei der Zersetzung der Diazoniumhalogenide

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Rates and pH-dependent product distributions of the CuCl2-catalyzed dediazoniation ofp-nitrobenzenediazonium tetrafluoroborate in aqueous acid

Bravo‐Díaz

Romsted

Harbowy

et al. 1999

J. Phys. Org. Chem.

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The rates of formation and yields of products from the dediazoniation of p-nitrobenzenediazonium tetrafluoroborate (PNBD) in aqueous solutions over a range of HCl, NaCl and CuCl 2 concentrations at 60°C were examined. Two main products were observed: p-nitrophenol (ArOH) and p-nitrochlorobenzene (ArCl). Trace amounts of nitrobenzene (ArH) and p-nitrofluorobenzene (ArF) were detected. Added CuCl 2 speeds the reaction and both the rate of dediazoniation and ArOH yield (unlike ArCl) are very sensitive to pH. The results are completely consistent with the heterolytic dediazoniation mechanism, i.e. rate-determining formation of a highly reactive aryl cation followed by competitive formation of dediazoniation products. PNBD kinetics are first order (with respect to PNBD) in the absence of and presence of CuCl 2 , except at low acidity and in the presence of low to moderate CuCl 2 concentrations. The non-first-order kinetics are attributed to a competing reaction between PNBD and the ArOH product. The results suggest a simple method for preparing halobenzenes in high yield.

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Rates and pH-dependent product distributions of the CuCl2-catalyzed dediazoniation ofp-nitrobenzenediazonium tetrafluoroborate in aqueous acid

Bravo‐Díaz

Romsted

Harbowy

et al. 1999

J. Phys. Org. Chem.

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Rundschau

1950

Angewandte Chemie

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Über die Sandmeyersche Reaktion III. Die Zersetzung von p‐Nitrobenzol‐diazoniumchlorid durch Kupfer(II)‐ und Eisen‐(III)chlorid

Pfeil

Velten

1949

Justus Liebigs Ann. Chem.

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Über die Sandmeyersche Reaktion I Die Bildung von Phenolen und Halogenbenzolen bei der Zersetzung der Diazoniumhalogenide

Cited by 3 publications

References 5 publications

Rates and pH-dependent product distributions of the CuCl2-catalyzed dediazoniation ofp-nitrobenzenediazonium tetrafluoroborate in aqueous acid

Rates and pH-dependent product distributions of the CuCl2-catalyzed dediazoniation ofp-nitrobenzenediazonium tetrafluoroborate in aqueous acid

Rundschau

Über die Sandmeyersche Reaktion III. Die Zersetzung von p‐Nitrobenzol‐diazoniumchlorid durch Kupfer(II)‐ und Eisen‐(III)chlorid

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Über die Sandmeyersche Reaktion I Die Bildung von Phenolen und Halogenbenzolen bei der Zersetzung der Diazoniumhalogenide

Cited by 3 publications

References 5 publications

Rates and pH-dependent product distributions of the CuCl2-catalyzed dediazoniation ofp-nitrobenzenediazonium ­tetrafluoroborate in aqueous acid

Rates and pH-dependent product distributions of the CuCl2-catalyzed dediazoniation ofp-nitrobenzenediazonium ­tetrafluoroborate in aqueous acid

Rundschau

Über die Sandmeyersche Reaktion III. Die Zersetzung von p‐Nitrobenzol‐diazoniumchlorid durch Kupfer(II)‐ und Eisen‐(III)chlorid

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Product

Resources

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Rates and pH-dependent product distributions of the CuCl2-catalyzed dediazoniation ofp-nitrobenzenediazonium tetrafluoroborate in aqueous acid

Rates and pH-dependent product distributions of the CuCl2-catalyzed dediazoniation ofp-nitrobenzenediazonium tetrafluoroborate in aqueous acid