Reaction of phenylhydrazines with arenes in the presence of aluminium trichloride

Authors
Ohwada, A Nara, S Sakamoto, T Kikugawa, Y
Citation
A. Ohwada et al., Reaction of phenylhydrazines with arenes in the presence of aluminium trichloride, J CHEM S P1, (22), 2001, pp. 3064-3068
Citations number
37
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
ISSN journal
14727781 → ACNP
Issue
22
Year of publication
2001
Pages
3064 - 3068
Database
ISI
SICI code
1472-7781(2001):22<3064:ROPWAI>2.0.ZU;2-Q
Abstract
Phenylnitrenium ions are generated from phenylhydrazines by treatment with AlCl3. Reaction of a phenylnitrenium ion with arenes results in both aromat ic N-substitution and C-substitution. In contrast, an N-methylphenylnitreni um ion undergoes exclusively aromatic C-substitution. Reaction of a phenyln itrenium ion with arenes present only in slight excess produces anilinated products in moderate to good yields.