Sandmeyer Reaction

• Aromatic Compounds
• Nucleic Acids

Aryl amines are converted to aryl halides

Sandmeyer Reaction

• Ar-NH2 -(Nitrous Acid)-> Ar-N2(+)
• Ar-N2(+) -(Lose N2)-> Ar-Meta(radical)
• Ar-Meta(radical) -(X)-> Ar-X
  • X = nucleophile: halides

Sandmeyer Reaction Fundamentals

Summary

• Oxidation reduction process
  • Aryl amines are converted into an electrophilic diazonium cation
  • Diazonium action reacts with a nucleophilic halogen
• Aryl halide is created

• Single electron transfer diazonium salt can be reduced to an arylndiazenyl radical
  • Quickly loses Nitrogens to create a Aryl radical intermediate
    • Aryl cation

Sandmeyer and DNA

• Adenine's NH2
• Guanine's NH2
• Cytosine's NH2
• Thymine's NH2

Sandmeyer and Proteins

Salient Examples:

• Bleomycin

Concepts:

• Redox Chemistry
• Transition Metal Nomenclature
  • Cupric vs Cuprous - Cu2 vs Cu1

Terminology:

• Arylamines - Phenyl/Aryl group attached to a NH2

Additional Information:

• Ochem.org