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  • 1
    ISSN: 0044-2313
    Keywords: Halomethylphosphonium Halides ; Bisphosphonium Salts ; Phosphoranylphosphonium Salts ; Transalkylation ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: On the Reaction of Halomethylphosphonium Halides, [R3PCYnX3-n]X, with Phosphanes, R′3PThe results of the reaction of 19 different halomethylphosphonium halides, [R3PCYnX3-n]X (R = Ph, n-Bu, Me2N, Et2N; Y = H, F; X = Cl, Br, I; n = 0-2), with Ph3P, n-Bu3P, and (R2N)3P are presented. As reaction products bisphosphonium salts, [R3P—CYnX2-n—PR′3]X2, and phosphoranylphosphonium salts, [R3P=CY—PR′3]X, or reduced (halo)methyl-phosphonium salts, [R3PCHYnX2-n]X, are obtained. [Ph3PCBrF2]Br and [Bu3PCBrF2]Br react with R′3P by trans-alkylation forming [R′3PCBrF2]Br. The factors influencing the course of the reaction are discussed.
    Notes: Es wird über die Reaktion von 19 verschiedenen Halomethylphosphoniumsalzen, [R3PCYnX3-n]X (R = Ph, n-Bu, Me2N, Et2N; Y = H, F; X = Cl, Br, I; n = 0-2), mit Ph3P, n-Bu3P und (R2N)3P berichtet. Als Reaktionsprodukte werden Bisphosphoniumsalze, [R3P—CYnX2-n—PR′3]X2, und Phosphoranylphosphoniumsalze, [R3P=CY—PR′3]X, oder reduzierte (Halo)methylphosphoniumsalze, [R3PCHYnX2-n]X, erhalten. [Ph3PCBrF2]Br und [Bu3PCBrF2]Br reagieren mit R′3P unter Umalkylierung zu [R′3PCBrF2]Br. Die den Reaktionsverlauf beeinflussenden Faktoren werden diskutiert.
    Additional Material: 5 Tab.
    Type of Medium: Electronic Resource
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  • 2
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Zeitschrift für anorganische Chemie 615 (1992), S. 66-72 
    ISSN: 0044-2313
    Keywords: Fluoridolysis ; oxidative fluorination ; fluorophosphates ; fluorophospholanes ; fluorospirophosphoranes ; triethylamin-HF-adducts ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Fluorination of Dioxa- and OxazaphospholanesThe fluoridolysis of cyclic esters and esteramides of phosphorous acid (1, 2, 4, 5, 7, 11, and 12,) using the acid fluorination reagent Et3N · nHF (n 〉 1) or an excess of a basic composed agent (n 〈 1) yields in all cases HPF5- (3,). With stoichiometric amounts of fluoride, however, the fluorophospholanes (4,) and (5,) as well as fac.- and mer.-o- (6a, 6b,) and the spirocyclic fluorohydridophosphate (8,) are obtained. (13,) reacts to (14,) and the spirocyclic compound (15,) gives (16,). The fluorophosphoranes (18,), (19,), and (21,) are obtained by oxidative fluorination of the spiro- or bicyclic P—H compounds 11, 12, and 20, with CCl4/Et3N · nHF (n 〈 1). The oxidative fluorination of the cyclic triesters of phosphorous acid 7, and 23, leads to the cyclic fluorophosphates (22,) and 16, as well as 6., The compounds 18, 19, and 22, are also formed by oxidative fluorination of elemental phosphorus, P4, in the presence of the corresponding bifunctional nucleophile.
    Notes: Die Fluoridolyse cyclischer Ester und Esteramide der phosphorigen Säure (1, 2, 4, 5, 7, 11, und 12,) mit dem sauren Fluorierungsagens Et3N · nHF (n 〉 1) ergibt ebenso wie mit überschüssigem basischen Fluorierungsmittel (n 〈 1) in allen Fällen HPF5- (3). Mit stöchiometrischen Mengen Fluorid werden dagegen die Fluorphospholane (4,) und (5,) sowie fac.- und mer.-o- (6a, 6b,) und das spirocyclische Fluorohydridophosphat (8,) erhalten. (13,) reagiert zu (14,) und die Spiroverbindung (15,) ergibt (16,). Durch oxidative Fluorierung mit der Reagenzkombination · nHF (n 〈 1) werden aus den spiro- bzw. bicyclischen P—H-Verbindungen 11, 12, und 20, die Fluorphosphorane (18,), (19,) und (21) erhalten. Die oxidative Fluorierung cyclischer Triester der phosphorigen Säure (7, 23,) führt zu den cyclischen Fluorophosphaten (22,) und 16, sowie 6., Die Verbindungen 18, 19, und 22, entstehen auch bei der oxidativen Fluorierung von P4 in Gegenwart des entsprechenden bifunktionellen Nucleophils.
    Additional Material: 4 Tab.
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