The heterocyclic ring of 4-substituted-1,8-naphthalimides is NOT inert to nucleophilic attack, contrary to earlier reports.
Org Biomol Chem
; 11(26): 4390-6, 2013 Jul 14.
Article
em En
| MEDLINE
| ID: mdl-23712745
ABSTRACT
The heterocyclic ring of N-aryl-4-chloro-1,8-naphthalimides, reported to be resistant to nucleophilic attack, reacts with primary amine nucleophiles at room temperature to give 4-chloro-N-alkyl-1,8-naphthalimides. The reaction is first order in the naphthalimide. The Hammett plot is linear (R(2) 0.996) with a large positive slope (+3.0), consistent with substantial negative charge development at nitrogen in the activated complex.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Naftalimidas
/
Aminas
Idioma:
En
Revista:
Org Biomol Chem
Ano de publicação:
2013
Tipo de documento:
Article