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

Molecular Rearrangement. 36. Selective α-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...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of organic chemistry 2004-10, Vol.69 (20), p.6706-6710
1. Verfasser: Badr, Mahmoud Z. A
Format: Artikel
Sprache:eng
Schlagworte:
Chemistry
Exact sciences and technology
Kinetics and mechanisms
Organic chemistry
Reactivity and mechanisms
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo040176+