Synthesis of a functional C-2-symmetrical bidentate diphenylphosphonite DIOP derivative and its conversion into the corresponding pi-acidic bis(pentafluorophenyl) and bis(p-tetrafluoropyridyl) compounds

Hoge B; Panne P

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Synthesis of a functional C-2-symmetrical bidentate diphenylphosphonite DIOP derivative and its conversion into the corresponding pi-acidic bis(pentafluorophenyl) and bis(p-tetrafluoropyridyl) compounds

机译：功能性C-2-对称双齿二苯基膦酸酯DIOP衍生物的合成及其转化为相应的pi酸性双（五氟苯基）和双（对四氟吡啶基）化合物

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The reaction of a C-2-symmetric diiodo compound, 1,4-dideoxy-1,4-diiodo-2,3,-O-isopropyliden-L-threitole, with [K([18]crown-6)]P(CN)(2) led to the generation of a corresponding bidentate dicyanophosphorus derivative. The in situ reaction with excess methanol and phenol yielded the corresponding bidentate dimethyl- and diphenylphosphonites, respectively. The isolated liquids were characterized by multinuclear NMR spectroscopy, elemental analysis, and mass spectrometry. The bidentate diphenylphosphonite ligand (a diphenoxyphosphane derivative) represents one of the very few functional bidentate phosphane derivatives: a DIOP [(2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(methylene)]bis(diphenyl- phosphane) modification, in which the phenyl groups at the phosphorus atoms are replaced by functional phenoxy groups. Treatment of the bidentate diphenylphosphonite derivative with C5F5MgBr and p-C5NF4MgBr allowed the isolation and full characterization of the comparable bidentate bis(pentafluorophenyl) and bis(p-tetrafluoropyridyl) phosphanes. The ligand properties of the novel bidentate ligand systems were evaluated through the synthesis and vibrational investigation of their tetracarbonyl-molybdenurn and cyclopentadienyl-iron complexes. The pi acidity of the synthesized ligands increases in the order methoxy-< phenoxy-< pentafluorophenyl-< p-tetrafluoropyridyl phosphane.

机译：C-2-对称二碘化合物，1,4-二脱氧-1,4-二碘-2,3，-O-异亚丙基-L-苏糖醇与[K（[18] crown-6）] P的反应（CN）（2）导致生成相应的二齿二氰基磷衍生物。与过量甲醇和苯酚的原位反应分别产生相应的二齿二甲基膦酸酯和二苯基膦酸酯。分离出的液体通过多核NMR光谱，元素分析和质谱进行表征。双齿二苯基膦酸酯配体（二苯氧基膦衍生物）代表极少数功能性双齿膦衍生物之一：DIOP [（（2,2-二甲基-1,3-二氧戊环-4,5-二基）双（亚甲基）]双（二苯基） -膦）改性，其中磷原子上的苯基被官能苯氧基取代。用C5F5MgBr和对-C5NF4MgBr处理二齿二苯基膦酸酯衍生物可以分离和完全表征可比的二齿双（五氟苯基）和双（对四氟吡啶基）膦。通过合成和振动研究其四羰基-钼和环戊二烯基-铁配合物，评估了新型双齿配体体系的配体性质。合成的配体的π酸度以甲氧基-<苯氧基-<五氟苯基-<对-四氟吡啶基膦的顺序增加。

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《Chemistry: A European journal》 |2006年第35期|共11页
作者
Hoge B; Panne P;
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正文语种 eng
中图分类化学;
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chirality; Lewis acids; P ligands; phosphonite; phosphanide; IRON LEWIS-ACID; ASYMMETRIC HYDROGENATION; COORDINATION CHEMISTRY; CATALYZED-REACTIONS; AROMATIC-ALDEHYDES; CRYSTAL-STRUCTURE; COMPLEXES; LIGANDS; DICYANOPHOSPHIDE; PHOSPHINES;

机译：手性;路易斯酸;P配体;亚膦酸酯;亚膦酸酯;铁路易斯酸;不对称加氢;配位化学;催化反应;芳族缩醛;晶体结构;化合物;化合物;对苯二甲酸;

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Synthesis of a functional C-2-symmetrical bidentate diphenylphosphonite DIOP derivative and its conversion into the corresponding pi-acidic bis(pentafluorophenyl) and bis(p-tetrafluoropyridyl) compounds

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