2-Substituted and 1,2-disubstituted indoles react with m-chloroperbenzoic acid and hydrogen peroxide in the presence of acid or calcium chloride affording 2- and 3-(3-oxoindol-2-yl)indoles; whereas 2,3-disubstituted indoles, reacting with the same oxidants, lead to the formation of products typical of pentaatomic ring opening. The reaction mechanisms are discussed in terms of electron transfer processes based on the redox potentials of the reagents, the Marcus theory and the reaction products distribution. The reactions of 1-hydroxy-2-phenylindole, which yield 2-phenylisatogen (2-phenyl-3-oxo-3H-indole 1-oxide), bisnitrone and 3-(3-oxoindol-2-yl)indole are also explained by an electron transfer mechanism depending on the oxidant and on the conditions of the reaction, The structures of 2- and 3-(3-oxoindol-2-yl)indoles have been elucidated by X-ray analysis.

Radical intermediates in the peroxidation of indoles / P., Astolfi; L., Greci; Rizzoli, Corrado; P., Sgarabotto; G., Marrosu. - In: JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS 2. - ISSN 1472-779X. - (2001), pp. 1634-1640. [10.1039/b102915k]

Radical intermediates in the peroxidation of indoles

RIZZOLI, Corrado;
2001-01-01

Abstract

2-Substituted and 1,2-disubstituted indoles react with m-chloroperbenzoic acid and hydrogen peroxide in the presence of acid or calcium chloride affording 2- and 3-(3-oxoindol-2-yl)indoles; whereas 2,3-disubstituted indoles, reacting with the same oxidants, lead to the formation of products typical of pentaatomic ring opening. The reaction mechanisms are discussed in terms of electron transfer processes based on the redox potentials of the reagents, the Marcus theory and the reaction products distribution. The reactions of 1-hydroxy-2-phenylindole, which yield 2-phenylisatogen (2-phenyl-3-oxo-3H-indole 1-oxide), bisnitrone and 3-(3-oxoindol-2-yl)indole are also explained by an electron transfer mechanism depending on the oxidant and on the conditions of the reaction, The structures of 2- and 3-(3-oxoindol-2-yl)indoles have been elucidated by X-ray analysis.
2001
Radical intermediates in the peroxidation of indoles / P., Astolfi; L., Greci; Rizzoli, Corrado; P., Sgarabotto; G., Marrosu. - In: JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS 2. - ISSN 1472-779X. - (2001), pp. 1634-1640. [10.1039/b102915k]
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/11381/1460851
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 29
  • ???jsp.display-item.citation.isi??? 27
social impact