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  • 1
    Electronic Resource
    Electronic Resource
    Neue σ2λ3-P=C - O-Systeme: Stabile nichtkonjugierte Phosphaalkenether - Synthese und Reaktionen (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 493-496 
    Details
    ISSN: 0009-2940
    Keywords: Phosphaalkene ethers ; 1,3-Oxaphospholes, dihydro- ; 1,3-Oxaphosphorines, tetrahydro- ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: New σ2λ3-P=C - O Systems: Stable Non-Conjugated Phosphaalkene Ethers - Synthesis and ReactivityNon-conjugated cyclic phosphaalkene ethers (2, 4, 6) are obtained by cyclocondensation of (2- or 3-hydroxyalkyl)phosphanes 1, 3 with N-arylpivalimidoyl chlorides. Hydrolysis of 2, 4 with H2O (→7, 8), addition of hydrogen compounds (HCl, HSPh, MePhPH) (→ 9-12), and oxidation with air (→ 14) are studied. The reactivity of the title compounds and of benzoxaphospholes are compared.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19911240312
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  • 2
    Electronic Resource
    Electronic Resource
    P/O Ligand Systems: Synthesis, Reactivity, and Structure of Tertiary o-Phosphanylphenol Derivatives (1997)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 130 (1997), S. 431-431 
    Details
    ISSN: 0009-2940
    Keywords: o-Phosphanylphenols ; P,O hybrid ligands ; P asymmetry ; C,O-dilithium reagents ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19971300320
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  • 3
    Electronic Resource
    Electronic Resource
    P/O Ligand Systems: Facile Synthesis, Structure, and Catalytic Tests of 2′-Phosphanyl-1,1′ -phenyl-2-ols and 2′-Phosphanyl-1,1′-binaphthyl-2-ols (1997)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 130 (1997), S. 1663-1670 
    Details
    ISSN: 0009-2940
    Keywords: Lithiation ; P ligands ; NMR spectroscopy ; Molecular structure ; Hydrogenations ; Hydroformylations ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A facile synthesis of 2′-phosphanyl-1,1′-biphenyl- and 2′-phosphanyl-1,1′ -binaphthyl-2-ols and their silyl ethers has been developed, consisting of electron-transfer-catalyzed ring-opening of dibenzofuran and dinaphthofuran, respectively, subsequent reaction with chlorophosphanes, and work-up with acetic acid or ClSiMe3. Studies of the molecular and crystal structures reveals the presence of P - H - O bridging bonds in the more basic tBuPhP derivative and a nearly perpendicular arrangement of the aryl planes in the biphenyl derivatives. The barrier to rotation of the aryl planes about the C-C axis was determined by NMR in the case of the P-asymmetric derivative 3d, using the appearence of diastereoisomers by atropisomerism and P-asymmetry. Comparative screening tests of the title compounds, phosphanyl phenols and phosphanylnaphthols in homogeneous Rh-catalyzed reactions demonstrate catalytic activity in hydroformylation reactions and superior properties of the biphenyl- and binaphthyl-2-ol derivatives in relation to other P-O ligands.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19971301118
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  • 4
    Electronic Resource
    Electronic Resource
    Syntheses, Structures, and Reactivity of 1-Phosphanylnaphth-2-ols (1996)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 129 (1996), S. 1061-1071 
    Details
    ISSN: 0009-2940
    Keywords: Phosphanylnaphthol ; PO ligands ; Chelate complexes ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: P-tertiary or amino-substituted 1-phosphanylnaphth-2-yl silyl ethers 3 are synthesized by stepwise reaction of lithium 1-lithio-2-naphtholate 1 with chlorophosphanes and ClSiMe3. The free phosphanylnaphthols 4 are prepared by alcoholysis. As established by characteristic coupling constants and X-ray structural analyses (of 3c, 4c), 3 exhibit in solution and in the solid state a cis-bisecting conformation, whereas 4 prefers the opposite trans-bisecting arrangement, allowing easy protonation and formation of chelate complexes. Substitution reactions of phosphanylnaphtholates 2 with Ph2PCl and formation of chelate complexes LNi-η5-Cp and L2Pd are described. Attempts to prepare secondary and primary phosphanylnaphthols failed because of facile cleavage of the P-C(naphthyl) bond in PH-substituted 1-phosphanylnaphth-2-ols.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19961290914
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  • 5
    Electronic Resource
    Electronic Resource
    P/O Ligand Systems: Synthesis, Reactivity, and Structure of Tertiary o-Phosphanylphenol Derivatives (1996)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 129 (1996), S. 1547-1560 
    Details
    ISSN: 0009-2940
    Keywords: o-Phosphanylphenols ; P,O hybrid ligands ; P asymmetry ; C,O-dilithium reagents ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Reactions of C,O-dilithium reagents 1 (M = M′ = Li) or C,O-lithium-sodium reagents 1 (M = Li, M′ = Na) with chlorophosphanes afford C,O-disubstitution products 2 or phosphanylphenolates 3 which are treated subsequently with ClSiMe3 to give 4-methyl- and bulky 4,6-di-tert-butyl substituted o-phosphanylphenol silyl ethers 4. These were applied for the preparation of the corresponding o-phosphanylphenols 5, mainly P-asymmetric derivatives. Limitations and side reactions by use of 1 in the above synthesis are discussed. Acid-base properties, pH-dependent solubility in water/hexane, and substitution reactions at oxygen and phosphorus of selected representatives of 5 are reported. An example for the separation of enantiomers by esterification with (1S)-(—)-camphanic acid chloride is given. IR studies revealed intramolecular P-H—O bonds and 2J(PC) the preferred trans arrangement of the phenoxy group in solution. In the solid state, inter- and intramolecular P-H—O bonds were detected by X-ray structure analysis. The trans arrangement of the phenoxy group is preserved. Because of steric hindrance, the O substituents are tilted towards the phosphorus atom and thus induce large through-space coupling constants. The P-Sn distance of 336.9 pm in the bulky substituted O—SnMe3 moiety 8h is however too large for the formation of genuine intramolecular coordination. The versatility of o-hydroxyarylphosphanes and objectives of further studies are shown by preliminary results on complex formation and applications of these phosphanes in catalysis.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19961291223
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