Synthèse de N-Alkyl-arylamines par Thermolyse ou Photolyse d'Alkyl-3-diaryl-1,3-triazènes

✍ Scribed by Par Michel Julliard; Gaston Vernin; Jacques Metzger

• Publisher: John Wiley and Sons
• Year: 1980
• Tongue: German
• Weight: 338 KB
• Volume: 63
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.19800630217

✦ Synopsis

Synthesis of N‐Alkyl‐arylamines by Thermolysis or Photolysis of 3‐Alkyl‐1,3‐bis(p‐chlorophenyl)triazenes

The thermolysis of 3‐alkyl‐1,3‐bis(p‐chlorophenyl)triazenes in benzene or methanol leads to the formation of N‐alkyl‐p‐chloroanilines (2) in 19–50% yield, N‐alkyl‐bis(p‐chlorophenyl)amines (3) in 7.5–15.5% yield and 4,4′‐dichlorobiphenyle (4) in 1–7% yield; besides with benzene as the substrate, 4‐chlorobiphenyle (5) (12–20% yield) was also formed. The photolysis in methanol gives only the N‐alkyl‐p‐chloroanilines (2) in 32–40% yield. In these two cases the results are consistent with a radical pair formation in a solvent cage, recombination (thermolysis) and/or diffusion (thermolysis and photolysis) with intermolecular abstraction of hydrogen. A free radical chain mechanism is involved in the photolytic process and the quantum yield is high.