Molecular Rearrangement. 36. Selective α-CH Oxidation of Alkylarenes by Nitrogen Dioxide on Thermolysis with Nitramines

Abstract

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.