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  • 1
    Electronic Resource
    Electronic Resource
    Novel Syntheses of Mono- and Bisphosphonated Aromatic Phosphanes by Consecutive Pd-Catalyzed P-C Coupling Reactions and Nucleophilic Phosphanylation - X-ray Structure of Ph2P-C6H4-m-PO3Na2 · 5.5 H2O · iPrOH (1998)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 1998 (1998), S. 1029-1034 
    Details
    ISSN: 1434-1948
    Keywords: Pd-catalyzed P-C coupling ; Nucleophilic phosphanylation ; Mono- and bisphosphonated phosphanes ; Monoesters ; Water solubility ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The triphenylphosphane derivatives 2a and 5, bearing one and two phosphonic ester groups, are accessible in high yields by consecutive Pd-catalyzed P-C coupling reactions of p-bromoiodobenzene with Ph2PH and PhPH2, respectively, and then with diethyl phosphite. Ester hydrolysis yields the highly water-soluble sodium salts of mono- and bis-phosphonated triphenylphosphane, 3a and 6, respectively. On reaction of the p- and m-fluorophenylphosphonic diethyl esters 7a, 7b with Ph2PK and subsequent ester hydrolysis the isomeric disodium (diphenylphosphano)phenylphosphonates 3a, 3b were obtained. The X-ray structure of Ph2P(C6H4-m-PO3Na2) · 5.5 H2O · iPrOH (space group Cmc21) has been determined. In the solid state, it forms a layer structure with hydrophilic (PO32-, H2O, iPrOH) and hydrophobic (Ph2P) compartments, in which the PO32- anionic groups are not engaged in coordination of the sodium cations.
    Type of Medium: Electronic Resource
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  • 2
    Electronic Resource
    Electronic Resource
    Nucleophilic Phosphanylation of Fluoroaromatic Compounds with Carboxyl, Carboxymethyl, and Aminomethyl Functionalities - an Efficient Synthetic Route to Amphiphilic Arylphosphanes (1998)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 1998 (1998), S. 73-82 
    Details
    ISSN: 1434-1948
    Keywords: Nucleophilic phosphanylation ; Phosphanylphthalic acid ; Phosphanylphenylacetic acid ; Benzylaminophosphanes ; Water solubility ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Chiral- and multiply-carboxylated phosphanes and phosphanyl derivatives of benzoic and phthalic acids (1-9) are accessible in high yields by nucleophilic phosphanylation of potassium or lithium salts of commercially available fluorobenzoic and 3-fluorophthalic acids with Ph2PH, Ph2PK, PhPLi2 Ph(K)P-(CH2)3-P(K)Ph in superbasic media (DMSO/KOH) or in THF and DME. The hitherto unknown phosphanylphenylacetic acids (10-13) and phosphanylbenzylamines RR′P-C6H4-CH2- NH2 (14-19, R, R′ = H, Me, Ph) with unsubstituted amino groups were also synthesized by this method. The diphenylphosphanyl derivatives 14-16 (R, R′ = Ph) are accessible by an alternative method involving LiAlH4 reduction of the phosphanylbenzonitriles (20-22), which were obtained in high yields by nucleophilic phosphanylation of the corresponding fluoro- or chlorobenzonitriles. The novel bidentate phosphanylbenzonitrile 23 has also been obtained using this synthetic route. All compounds were completely characterized by elemental analysis, NMR spectroscopy, and mass spectrometry.
    Type of Medium: Electronic Resource
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