Molecular rearrangement. 36. Selective alpha-CH oxidation of alkylarenes by nitrogen dioxide on thermolysis with nitramines.
Thermolysis of 2,4,6-trichloro-N-nitroaniline 1 and N-methyl-2,4-dinitro-N-nitroaniline 2 each with primaryl alkylbenzenes led to the formation of acylbenzenes. Similar reactions with secondary alkylbenzenes afforded a mixture of acetophenone and aliphatic aldehydes. Use of tert-butylbenzene in this reaction yielded formaldehyde and 2,3-diphenyl-2,3-dimethylbutane. The mechanisms of the studied reactions are discussed.
Badr
Mahmoud Z A
MZ
Chemistry Department, Faculty of Science, Assiut University, Assiut, Egypt. m.z.badr@acc.aun.edu.eg