Synthese de N-Alkyl-arylamines par Thermolyse ou Photolyse d'Alkyl-3-diaryl-1,3-triazenes

Article abstract of DOI:10.1002/hlca.19800630217

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 percent yield, N-alkyl-bis(p-chlorophenyl)amines (3) in 7.5-15.5 percent yield and 4,4'-dichlorobiphenyle (4) in 1-7 percent yield; besides with benzene as the substrate, 4-chlorobiphenyle (5) (12-20 percent yield) was also formed.The photolysis in methanol gives only the N-alkyl-p-chloroanilines (2) in 32-40 percent 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.