Noncovalent sulfur···oxygen interactions can increase the stability of chalcogen ortho-substituted phenoxyl radicals. This effect contributes to transforming the 7-hydroxybenzo[b]thiophene moiety in a privileged structural motif to enhance the activity of phenolic antioxidants. A cascade of five consecutive electrophilic reactions occurring in one pot afforded potent and biocompatible α-tocopherol-like antioxidants.
Role of Noncovalent Sulfur···Oxygen Interactions in Phenoxyl Radical Stabilization: Synthesis of Super Tocopherol-like Antioxidants / Menichetti, S; Amorati, R; Meoni, V; Tofani, L; Caminati, G; Viglianisi, C. - In: ORGANIC LETTERS. - ISSN 1523-7060. - STAMPA. - (2016), pp. 5464-5467. [10.1021/acs.orglett.6b02557]
Role of Noncovalent Sulfur···Oxygen Interactions in Phenoxyl Radical Stabilization: Synthesis of Super Tocopherol-like Antioxidants
MENICHETTI, STEFANO
;TOFANI, LORENZO;CAMINATI, GABRIELLA;VIGLIANISI, CATERINA
2016
Abstract
Noncovalent sulfur···oxygen interactions can increase the stability of chalcogen ortho-substituted phenoxyl radicals. This effect contributes to transforming the 7-hydroxybenzo[b]thiophene moiety in a privileged structural motif to enhance the activity of phenolic antioxidants. A cascade of five consecutive electrophilic reactions occurring in one pot afforded potent and biocompatible α-tocopherol-like antioxidants.File | Dimensione | Formato | |
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