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  • Halomethylphosphonium Halides  (1)
  • Phosphonothionic esters  (1)
  • 1990-1994  (2)
  • 1
    Electronic Resource
    Electronic Resource
    Zur Reaktion von Halomethylphosphoniumhalogeniden, [R3PCYnX3-n]X, mit Phosphanen, R′3P (1994)
    Weinheim : Wiley-Blackwell
    Zeitschrift für anorganische Chemie 620 (1994), S. 1103-1109 
    Details
    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
    URL: http://dx.doi.org/10.1002/zaac.19946200626
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  • 2
    Electronic Resource
    Electronic Resource
    Darstellung und oxidative Derivatisierung von Dialkylthiophosphiten (1992)
    Weinheim : Wiley-Blackwell
    Zeitschrift für anorganische Chemie 617 (1992), S. 148-154 
    Details
    ISSN: 0044-2313
    Keywords: Phosphonothionic esters ; preparation ; oxidation with carbon tetrachloride ; thiophosphoric acid derivatives ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Preparation and Oxidative Derivatisation of Phosphonothionic EstersThe kind of the amine used influences decisively course and rate of the reaction of trialkyl phosphites, (RO)3P (R = Me, Et, Ph) with H2S in the presence of different amines (Et3N, Et2NH, Et2NPh, pyridine). Phosphonothionic esters, (RO)2P(S)H (R = Me, Et, Bu), are obtained in over 80% yield by using pyridine as base and an alkali alcoholate as catalyst. The oxidative derivatisation of phosphonothionic esters by means of CCI4 and protic (4-nitrophenol, 2,4,5-trichlorophenol, ammonia, piperidine, phenylhydrazine) or anionic nucleophiles (F-, NCS-, NCO-, CN-, N3-) (Atherton-Todd reaction) yields thiophosphoric acid derivatives (RO)2P(S)Nuc (R = Me, Et, Bu: Nuc = 4-nitrophenoxy, PhNHNH; R = Me, Et: Nuc = 2,4,5-trichlorophenoxy, F, NCS, N3; R = Me: NH2, C5H10N; R = Et: Nuc = CI, CN) and in some cases the dealkylated products (RO)P(Nuc)SO- (R = Me; Nuc = CI, F, NCS, CN). The phosphazenes (EtO)2P(S)—N = PPh3 and (MeO)2P(S)—N = P(OEt)3, up to now unknown in literature, were obtained by treating thiophosphoryl azides with PPh3 or P(OEt)3, resp.
    Notes: Geschwindigkeit und Verlauf der Reaktion von Triestern der phosphorigen Säure, (RO)3P (R = Me, Et, Ph) mit H2S in Gegenwart verschiedener Amine (Et3N, Et2NH, Et2NPh, Pyridin) werden entscheidend von der Art des verwendeten Amins beeinflußt. Bei Verwendung von Pyridin als Base und Alkalialkoholaten als Katalysatoren werden Thiophosphorigsäuredialkylester, (RO)2P(S)H (R = Me, Et, Bu), mit über 80% Ausbeute erhalten. Die oxidative Derivatisierung der Thiophosphite mit CCI4 und protischen (4-Nitrophenol, 2,4,5-Trichlorphenol, Ammoniak, Piperidin, Phenylhydrazin) bzw. anionischen Nucleophilen (F-, NCS-,NCO-, CN-, N3-), (Atherton-Todd-Reaktion) ergibt Thiophosphorsäurederivate (RO)2P(S)Nuc (R = Me, Et, Bu: Nuc = 4-Nitrophenoxy, PhNHNH; R =; Me, Et: Nuc = 2,4,5-Trichlorphenoxy, F, NCS, N3; R = Me: NH2, C5H10N; R = Et: Nuc = CI, CN) und z. T. deren Entalkylierungsprodukte (RO)P(Nuc)SO- (R = Me; Nuc = CI, F, NCS, CN). Die Umsetzung der Thiophosphorylazide mit PPh3 bzw. P(OEt)3 ermöglichte die Darstellung der noch nicht beschriebenen Phosphazene (EtO)2P(S)—N = PPh3 und (MeO)2P(S)—N = P(OEt)3.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/zaac.19926170126
    Location Call Number Expected Availability
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    Paper (German National Licenses)
    Fulltext
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