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  • 1
    ISSN: 0021-8383
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: α-Substituted Phosphonates. XXXI. The Reaction of N,N,N′,N′-Tetramethyl Chloroformamidinium Chloride with P(III) CompoundsN,N,N′,N′-Tetramethyl chloroformamidiniumchloride (4) does not react with triethyl phosphite (TEP) or isopropyl diphenylphosphinate to give the expected bisphosphoryl derivatives 7 and 11, respectively, but primarily the monophosphorylated amidinium salts 6 and 10 respectively. The phosphine oxide 10 is stable, while 6 undergoes an elimination of ethyl chloride to the betain 8. Even under more drastic conditions the reaction of 4 or 8 with TEP does not lead to the expected bis(dimethylamino)bisphosphonate 7, but to the monoaminated bisphosphonate 1, involving a reduction step. Similar reduction has been observed under mild conditions in Michaelis-Arbusov reaction of dichloromethylenimonium chloride, yielding the expected trisphosphonate 2 and the bisphosphonate 1 as a by-product.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
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  • 2
    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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