Nucleophilic character of alkyl radicals. XIV. Homolytic δ‐aminoalkylation of protonated quinoxaline | Zendy

Caronna T. | Zendy; Citterio A. | Zendy; Crolla T. | Zendy; Ghirardini M. | Zendy; Minisci F. | Zendy

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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.

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