Selective homolytic alkylation of protonated quinoxaline has been achieved by using an alkyl derivative with N-chlorodialkylamine as radical source. The method shows great synthetic potential and can also be used for other heteroaromatic bases. A free-radical chain process involving amine radical cations is suggested to explain the clean reaction. Positional selectivity is strongly affected by the medium acidity, and a correlation between the π-electron density of mono- and di-protonated quinoxaline and the substitution orientation is found, in agreement with the nucleophilic character of the alkyl radicals.

Nucleophilic character of alkyl radicals. Part 15. Selective homolytic alkylation of quinoxaline by N-chloro-amines; influence of medium acidity

Caronna, T.;Citterio, A.;Minisci, F.
1977-01-01

Abstract

Selective homolytic alkylation of protonated quinoxaline has been achieved by using an alkyl derivative with N-chlorodialkylamine as radical source. The method shows great synthetic potential and can also be used for other heteroaromatic bases. A free-radical chain process involving amine radical cations is suggested to explain the clean reaction. Positional selectivity is strongly affected by the medium acidity, and a correlation between the π-electron density of mono- and di-protonated quinoxaline and the substitution orientation is found, in agreement with the nucleophilic character of the alkyl radicals.
1977
Organic Chemistry, Free Radicals, homolytic Alkylation, heteroaromatic bases, N-chloroamines
File in questo prodotto:
Non ci sono file associati a questo prodotto.

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11311/1047381
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 20
  • ???jsp.display-item.citation.isi??? ND
social impact