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  • 1,5-diphosphabicyclo[3.3.1]nonanes  (1)
  • 1-phosphabicyclo[3.3.1]nonanes  (1)
  • 1-phosphabicyclo[4.3.0]nonanes  (1)
  • 1
    Electronic Resource
    Electronic Resource
    1,5-Diphosphabicyclo[3.3.1]nonanFrau Professor Marianne Baudler zum 70. Geburtstage am 27. April 1991 gewidmet (1991)
    Weinheim : Wiley-Blackwell
    Zeitschrift für anorganische Chemie 594 (1991), S. 66-76 
    Details
    ISSN: 0044-2313
    Keywords: Organophosphorus compounds, bicyclic hydrophosphorylation, intramolecular ; methylenebisphosphines ; 1,3-diphosphorinances ; 1,5-diphosphabicyclo[3.3.1]nonanes ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: 1,5-Diphosphabicyclo [3.3.1]nonane1,5-Diphosphabicyclo[3.3.1]nonane 8 has been obtained by free-radical cyclization of CH2=CHCH2(H)PCH2P(H)CH2CH=CH2 6 and 1-allyl-1,3-diphosphorinane 7. For the synthesis of 6 and 7 the chlorophosphine Cl2PCH2PCl2 1 is used as a starting material, which can be converted into Me2N(Cl)PCH2P(Cl)NMe2 3 by reaction with (Me2N)2PCH2P(NMe2)2 2. Treatment of 3 with two equivalents of allyl lithium and cleavage of the PN bonds in CH2=CHCH2(Me2N)PCH2P(NMe2)CH2CH=CH2 4 with diluted HCl affords CH2=CHCH2(H)(O)PCH2P(O)(H)CH2CH=CH2 5. Phenylsilane is used for the first time as a reducing agent to obtain a secundary phosphine like 6 from the secundary phosphine oxide (5). Prolonged heating increases the yield of the byproduct 7 in the mixture of 6 and 7. Reactions of the trivalent phosphorus in 8 with CS2, CH3I, POCl3, NO, sulfur, and KSeCN, respectively, delivers the corresponding derivatives 9-17. The compounds decribed are characterized by 1H, 13C, 31P, 77Se n.m.r., i.r., and m.s. data.
    Notes: 1,5-Diphosphabicyclo[3.3.1]nonan 8 wird durch radikalische Cyclisierung von CH2=CHCH2(H)PCH2P(H)CH2CH=CH2 6 und 1-Allyl-1,3-diphosphorinan 7 erhalten. Ausgangsmaterial für die Synthese von 6 und 7 ist Cl2PCH2PCl2 1, das mit (Me2N)2PCH2P(NMe2)22 quantitativ zu Me2N(Cl)PCH2P(Cl)NMe2 3 reagiert. Die Umsetzung von 3 mit zwei Äquivalenten Allyllithium zu CH2=CHCH2(Me2N)PCH2P(NMe2)CH2CH=CH2 4 und Abspaltung der Me2N-Schutzgruppen mit verdünnter Salzsäure liefert CH2=CHCH2(H)(O)PCH2P(O)(H)CH2CH=CH2 5. Dessen Reduktion zu 6 gelingt mit C6H5SiH3. Daneben entsteht 7, das durch längeres Erhitzen angereichert werden kann. Reaktionen des dreibindigen Phosphors in 8 mit CS2, CH3I, POCl3, NO, Schwefel und KSeCN führen zu den Derivaten 9-17. Die Verbindungen werden durch 1H-, 13C-, 31P- und 77Se-NMR-sowie IR- und MS-Daten charakterisiert.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/zaac.19915940108
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  • 2
    Electronic Resource
    Electronic Resource
    Cis-1-Phosphabicyclo[4.3.0]nonanProfessor Helmut Köhler in memoriam (1991)
    Weinheim : Wiley-Blackwell
    Zeitschrift für anorganische Chemie 600 (1991), S. 195-202 
    Details
    ISSN: 0044-2313
    Keywords: Intramolecular hydrophosphorylation ; bicyclic organophosphorus compounds ; 1-phosphabicyclo[4.3.0]nonanes ; conformational analysis ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Cis-1-Phosphabicyclo[4.3.0]nonanecis-1-Phosphabicyclo[4.3.0]nonane has been synthesized by free-radical cyclization of 4-phophino-octa-1.7-diene. The bicyclic phosphine is characterized by reactions with CS2, Ni(CO)4, HSO3F, CH3I, H2O2, sulfur, and selenium, respectively. The determination of the relative configuration of the phosphine is done by a qualitative conformational analysis from the 13C n.m.r. data.
    Notes: Durch radikalische Cyclisierung von 4-Phosphino-octa-1,7-dien erhält man cis-1-Phosphabicyclo [4.3.0]nonan, das durch Reaktionen mit CS2, Ni(CO)4, HSO3F, CH3I, H2O2, Schwefel und Selen charakterisiert wird. Die Bestimmung der relativen Konfiguration des Phosphins erfolgt durch eine qualitative Konfigurationsanalyse aus den 13C-NMR-Daten.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/zaac.19916000127
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  • 3
    Electronic Resource
    Electronic Resource
    5-Hydroxy-1-phosphabicyclo[3.3.1]nonanProfessor Heinrich Nöth zum 65. Geburtstage gewidmet (1993)
    Weinheim : Wiley-Blackwell
    Zeitschrift für anorganische Chemie 619 (1993), S. 989-992 
    Details
    ISSN: 0044-2313
    Keywords: Bicyclic organophosphorus compounds ; intramolecular hydrophosphorylation ; 1-phosphabicyclo[3.3.1]nonanes ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: 5-Hydroxy-1-phosphabicyclo[3.3.1]nonaneA new approach to 1-phosphabicyclo[3.3.1]nonane compounds involves free-radical cyclization of 4-trimethylsilyloxy-4-phosphinomethyl-hepta-1.6-diene synthesized by the reaction of 2.2-diallyl-oxirane with KPH2 followed by trimethylsilylation. Trimethylsilyl groups are easily cleaved in boiling methanol forming 5-hydroxy-1-phosphabicyclo[3.3.1]nonanes. Silylated and desilylated bicyclic compounds are characterized by n.m.r. and i.r. data.
    Notes: Die Reaktion von 2,2-Diallyl-oxiran mit KPH2 zu 4-Hydroxy-4-phosphinomethyl-hepta-1,6-dien, das nach Bildung des Trimethylsilylethers radikalisch cyclisiert wird, stellt einen neuen Zugang zum 1-Phosphabicyclo[3.3.1]nonan-System dar. Die Titelverbindung wird durch Abspaltung der Trimethylsilylgruppe in siedendem Methanol gebildet. Die silylierten und entsilylierten bicyclischen Verbindungen werden durch NMR- und IR-Daten charakterisiert.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/zaac.19936190605
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