Rahaman, Rubina published the artcileDioxygen reactivity of iron(II)-gentisate/1,4-dihydroxy-2-naphthoate complexes of N4 ligands: oxidative coupling of 1,4-dihydroxy-2-naphthoate, Synthetic Route of 86-48-6, the publication is Dalton Transactions (2019), 48(45), 16993-17004, database is CAplus and MEDLINE.
The influence of supporting ligands and co-ligands on the dioxygen reactivity of Fe(II) complexes, [(6-Me3-TPA)FeII(GN-H)]+ (1), [(6-Me3-TPA)FeII(DHN-H)]+ (1a), [(BPMEN)FeII(GN-H)]+ (2), [(BPMEN)FeII(DHN-H)]+ (2a), [(TBimA)FeII(GN-H)]+ (3), and [(TBimA)FeII(DHN-H)]+ (3a) (GN-H2 = 2,5-dihydroxybenzoic acid and DHN-H2 = 1,4-dihydroxy-2-naphthoic acid) of N4 ligands, is presented. The Fe(II)-gentisate complexes react with dioxygen to afford the corresponding Fe(III) species. On the contrary, DHN-H undergoes oxidative C-C coupling to form [2,2′-binaphthalene]-1,1′,4,4′-tetrone 3-hydroxy-3′-carboxylic acid (BNTHC) on 1a, and [2,2′-binaphthalene]-1,1′,4,4′-tetrone 3,3′-dicarboxylic acid (BNTD) on 2a and 3a. In each case, the reaction proceeds through an Fe(III)-DHN species. The x-ray single crystal structures of [(6-Me3-TPA)FeII(BNTD)] (1Ox) and [(BPMEN)FeII(BNTD)] (2Ox) confirm the coupling of two DHN-H mols. The formation of Fe(III) product without any coupling of co-ligand from the complexes, [(BPMEN)FeII(HNA)]+ (2b) and [(BPMEN)FeII(5-OMeSA)]+ (2c) (HNA = 1-hydroxy-2-naphthoate, 5-OMeSA = 5-methoxysalicylate) confirms the importance of para-hydroxy group for the coupling reaction. The unusual coupling of DHN-H by the Fe(II) complexes of the neutral N4 ligands is distinctly different from the oxygenolytic aromatic C-C cleavage of DHN by the Fe(II) complex of a facial N3 ligand.
Dalton Transactions published new progress about 86-48-6. 86-48-6 belongs to alcohols-buliding-blocks, auxiliary class Organic Pigment,Natural product, name is 1-Hydroxy-2-naphthoic acid, and the molecular formula is C11H8O3, Synthetic Route of 86-48-6.
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