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Nucleophilic character of alkyl radicals. XIV. Homolytic δ‐aminoalkylation of protonated quinoxaline
Author(s) -
Caronna T.,
Citterio A.,
Crolla T.,
Ghirardini M.,
Minisci F.
Publication year - 1976
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570130504
Subject(s) - chemistry , homolysis , quinoxaline , radical , nucleophile , hydrogen atom abstraction , intramolecular force , protonation , alkyl , medicinal chemistry , nucleophilic substitution , alkylation , selectivity , photochemistry , organic chemistry , catalysis , ion
A new general reaction of wide synthetic interest, involving homolytic δ‐aminoalkylation of quinoxaline in acidic medium, is described. Primary and secondary alkylamines, through the corresponding N ‐chloroamines, and tertiary alkylamines, through the corresponding N ‐oxides, 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.