The transformation of simple phenols with limited antioxidant activity into potent chain-breaking antioxidants was achieved by a three-step protocol, consisting of the conversion of phenols into 1,4-benzo[b]oxathiines followed by an unprecedented acid-promoted transposition to o-hydroxydihydrobenzo[b]thiophenes, or dihydrobenzo[de]thiochromenes, starting from phenols or naphthols, respectively. These derivatives, bearing a benzo-fused heterocycle with a sulfide sulfur ortho to the phenolic OH, have a rate constant of reaction with alkylperoxyl radicals (k(inh)) comparable to that of -tocopherol. A solid rationale for the transposition mechanism as well as for the structure-antioxidant activity relationship is presented

A Straightforward Route to Potent Phenolic Chain-Breaking Antioxidants by Acid-Promoted Transposition of 1,4-Benzo[b]oxathiines to Dihydrobenzo[b]thiophenes / Viglianisi, Caterina; Amorati, Riccardo; Di Pietro, Leonardo; Menichetti, Stefano. - In: CHEMISTRY-A EUROPEAN JOURNAL. - ISSN 0947-6539. - STAMPA. - 21:(2015), pp. 16639-16645. [10.1002/chem.201502650]

A Straightforward Route to Potent Phenolic Chain-Breaking Antioxidants by Acid-Promoted Transposition of 1,4-Benzo[b]oxathiines to Dihydrobenzo[b]thiophenes

VIGLIANISI, CATERINA;MENICHETTI, STEFANO
2015

Abstract

The transformation of simple phenols with limited antioxidant activity into potent chain-breaking antioxidants was achieved by a three-step protocol, consisting of the conversion of phenols into 1,4-benzo[b]oxathiines followed by an unprecedented acid-promoted transposition to o-hydroxydihydrobenzo[b]thiophenes, or dihydrobenzo[de]thiochromenes, starting from phenols or naphthols, respectively. These derivatives, bearing a benzo-fused heterocycle with a sulfide sulfur ortho to the phenolic OH, have a rate constant of reaction with alkylperoxyl radicals (k(inh)) comparable to that of -tocopherol. A solid rationale for the transposition mechanism as well as for the structure-antioxidant activity relationship is presented
2015
21
16639
16645
Viglianisi, Caterina; Amorati, Riccardo; Di Pietro, Leonardo; Menichetti, Stefano
File in questo prodotto:
File Dimensione Formato  
2015_Chem-A-EurJ_2015_21_16639-16645.pdf

Accesso chiuso

Descrizione: Reprint articolo
Tipologia: Pdf editoriale (Version of record)
Licenza: Tutti i diritti riservati
Dimensione 575.63 kB
Formato Adobe PDF
575.63 kB Adobe PDF   Richiedi una copia

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

Utilizza questo identificatore per citare o creare un link a questa risorsa: https://hdl.handle.net/2158/1038385
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 14
  • ???jsp.display-item.citation.isi??? 14
social impact