A new general reaction of wide synthetic interest, involving homolytic δâaminoalkylation of quinoxaline in acidic medium, is described. Primary and secondary alkylamines, through the corresponding Nâchloroamines, and tertiary alkylamines, through the corresponding Nâoxides, are used. The mechanism of the reaction, involving intramolecular hydrogen abstraction by amino radical cations, and the unusual selectivity are discussed in terms of nucleophilic character of the alkyl radicals and of polar effects in the aromatic substitution. Copyright © 1976 Journal of Heterocyclic Chemistry
Nucleophilic character of alkyl radicals. XIV. Homolytic 뫉aminoalkylation of protonated quinoxaline
Caronna, T.;Citterio, A.;Minisci, F.
1976-01-01
Abstract
A new general reaction of wide synthetic interest, involving homolytic δâaminoalkylation of quinoxaline in acidic medium, is described. Primary and secondary alkylamines, through the corresponding Nâchloroamines, and tertiary alkylamines, through the corresponding Nâoxides, are used. The mechanism of the reaction, involving intramolecular hydrogen abstraction by amino radical cations, and the unusual selectivity are discussed in terms of nucleophilic character of the alkyl radicals and of polar effects in the aromatic substitution. Copyright © 1976 Journal of Heterocyclic ChemistryFile in questo prodotto:
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