Synthetic Route of C38H24F4O4P2. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, is researched, Molecular C38H24F4O4P2, CAS is 503538-69-0, about Chiral biphenyl diphosphines for asymmetric catalysis: stereoelectronic design and industrial perspectives. Author is Jeulin, Severine; De Paule, Sebastien Duprat; Ratovelomanana-Vidal, Virginie; Genet, Jean-Pierre; Champion, Nicolas; Dellis, Philippe.
Both enantiomers of the chiral diphosphines I (SYNPHOS) and II (DIFLUORPHOS) are prepared on multigram scales; the electronic and steric characteristics of I and II and of rhodium complexes derived from them are determined, compared with previous diphosphine catalysts, and correlated with their activities and enantioselectivities in the hydrogenation of ketones and olefins. I and II are prepared in five steps from 6-bromo-2,3-dihydro-1,4-benzodioxane and 5-bromo-2,2-difluorobenzodioxole, resp.; lithium-metal exchange and addition to a phosphoryl or phosphinyl chloride followed by oxidation to yield phosphine oxides, regioselective lithiation and iodination, Ullman coupling of the aryl iodides, resolution (either by acid-base resolution with di-O-benzoyl-tartaric acid or by chiral HPLC), and reduction of the phosphine oxides yields I and II in 38% and 33% overall yield, resp. The bite angles of I and II are compared to those of other common diphosphine ligands such as BINAP and MeO-BIPHEP. The structure of diastereomeric chlorohydridoruthenium complexes of (S)-II with Me acetoacetate is determined The C-O stretching frequencies of chloro(carbonyl)rhodium diphosphine complexes containing I, II, BINAP, and MeO-BIPHEP are determined as a measure of the electronic demands of the diphosphine ligands. β-Keto ester, α-keto ester, 1,3-diketone, ketone, and olefin substrates are hydrogenated in the presence of nonracemic I, II, BINAP, and MeO-BIPHEP and bis(η3-methallyl)(η4-1,5-cyclooctadienyl)ruthenium; the enantioselectivities are correlated with the steric and electronic properties of the ligands. The stereoelectronic features of the ligand and the substrate deeply influence the enantioselectivities obtained in asym. hydrogenation; whereas the steric and electronic factors for I (as in other diphosphines) correlate well, the bite angle of II does not correlate to its electronic effects in asym. hydrogenation reactions, leading to complementary hydrogenation selectivities for ligands I and II.
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Reference:
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