A new general process of selective, homolytic alkylation of heteroaromatic bases of great synthetic interest is described. It is based on the reaction of alkyl iodides with hydrogen peroxide and heterocyclic compounds in DMSO, catalyzed by an Fe(II) salt. It is shown that the iodine abstraction from the alkyl iodide by the methyl radical, generated from the solvent, is the key point of the overall process. Combined enthalpic and polar effects contribute to the high selectivity: the enthalpic factor governs the equilibria of the iodine abstraction, and the polar factor determines the reactivity toward the protonated heterocyclic ring.

(1989). Homolytic Alkylation of Protonated Heteroaromatic Bases by Alkyl Iodides, Hydrogen Peroxide, and Dimethyl Sulfoxide [journal article - articolo]. In JOURNAL OF ORGANIC CHEMISTRY. Retrieved from https://hdl.handle.net/10446/231774

Homolytic Alkylation of Protonated Heteroaromatic Bases by Alkyl Iodides, Hydrogen Peroxide, and Dimethyl Sulfoxide

Fontana, Francesca
1989

Abstract

A new general process of selective, homolytic alkylation of heteroaromatic bases of great synthetic interest is described. It is based on the reaction of alkyl iodides with hydrogen peroxide and heterocyclic compounds in DMSO, catalyzed by an Fe(II) salt. It is shown that the iodine abstraction from the alkyl iodide by the methyl radical, generated from the solvent, is the key point of the overall process. Combined enthalpic and polar effects contribute to the high selectivity: the enthalpic factor governs the equilibria of the iodine abstraction, and the polar factor determines the reactivity toward the protonated heterocyclic ring.
articolo
Minisci, Francesco; Vismara, Elena; Fontana, Francesca
(1989). Homolytic Alkylation of Protonated Heteroaromatic Bases by Alkyl Iodides, Hydrogen Peroxide, and Dimethyl Sulfoxide [journal article - articolo]. In JOURNAL OF ORGANIC CHEMISTRY. Retrieved from https://hdl.handle.net/10446/231774
File allegato/i alla scheda:
File Dimensione del file Formato  
jo00283a011.pdf

Solo gestori di archivio

Versione: publisher's version - versione editoriale
Licenza: Licenza default Aisberg
Dimensione del file 564.22 kB
Formato Adobe PDF
564.22 kB Adobe PDF   Visualizza/Apri
Pubblicazioni consigliate

Caricamento pubblicazioni consigliate

Aisberg ©2008 Servizi bibliotecari, Università degli studi di Bergamo | Terms of use/Condizioni di utilizzo

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10446/231774
Citazioni
  • Scopus 77
  • ???jsp.display-item.citation.isi??? 78
social impact