Direct (uncatalysed) formation of Meisenheimer complexes from primary, secondary and tertiary arylamines

✍ Scribed by Robert J. Spear; William P. Norris; Roger W. Read

• Publisher: Elsevier Science
• Year: 1983
• Tongue: French
• Weight: 201 KB
• Volume: 24
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)81708-6

✦ Synopsis

Aniline, Ij-methylaniline and N,Ij-dimethylaniline react through their para positions with 4,6-dinitrobenzofurazanl-oxide to form stable Meisenheimer complexes.

Prior to 1972 it was thought that arylamines would not form stable Meisenheimer (or sigma) complexes with electron deficient aromatics but that only weak charge transfer complexes could be obtained. 2,3 However since 1972 Buncel and co-workers have achieved Meisenheimer complex formation between a series of primary4 and secondary5 aromatic amines and 1,3,5_trinitrobenzene (TNB) indirectly