title: Regenerable Thiophenolic Radical-Trapping Antioxidants.
abstract: Diphenyl disulfides carrying alkyltelluro groups in the o-, m-, and p-positions were prepared using ortho-lithiation and lithium halogen exchange reactions. The novel antioxidants showed only minimal inhibitory effect on the azo-initiated peroxidation of linoleic acid in chlorobenzene until reduced to the corresponding thiophenols by tris(2-carboxyethyl)phosphine (TCEP). The best in situ generated thiophenol (from 7c) under these conditions quenched peroxyl radicals more efficiently than α-tocopherol with an almost 3-fold increase in inhibition time.
authors.affiliation: Uppsala University , Department of Chemistry - BMC, Box 576, SE-751 23 Uppsala, Sweden.
authors.forename: Jiajie
authors.initials: J
authors.lastname: Yan
authors.affiliation: Uppsala University , Department of Chemistry - BMC, Box 576, SE-751 23 Uppsala, Sweden.
authors.forename: Jia-fei
authors.initials: JF
authors.lastname: Poon
authors.affiliation: Uppsala University , Department of Chemistry - BMC, Box 576, SE-751 23 Uppsala, Sweden.
authors.forename: Vijay P
authors.initials: VP
authors.lastname: Singh
authors.affiliation: University of Bristol , School of Chemistry, Bristol, BS8 1TS, United Kingdom.
authors.forename: Paul
authors.initials: P
authors.lastname: Gates
authors.affiliation: Uppsala University , Department of Chemistry - BMC, Box 576, SE-751 23 Uppsala, Sweden.
authors.forename: Lars
authors.initials: L
authors.lastname: Engman
mesh_terms: D000975:Antioxidants / Q000737:chemistry / Q000494:pharmacology*; D019787:Linoleic Acid / Q000737:chemistry; D015394:Molecular Structure; D010636:Phenols / Q000737:chemistry*; D010720:Phosphines / Q000737:chemistry*; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D024502:alpha-Tocopherol / Q000737:chemistry
chemical_list: D000975:Antioxidants; D019787:Linoleic Acid; D010636:Phenols; D010720:Phosphines; D013438:Sulfhydryl Compounds; D024502:alpha-Tocopherol; C080938:tris(2-carboxyethyl)phosphine; C042983:thiophenol