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  • 1
    ISSN: 0044-2313
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Oxidative Derivatization of 1,3,2-Dioxaphosphorinanes Using Carbon Tetrachloride as Oxidant2-Alkoxy- and 2-dialkylamido-1,3,2-dioxaphosphorinanes react with CCl4 in presence or absence of protic nucleophiles under ring opening forming acyclic derivatives of phosphates. 2-Anilido-1,3,2-dioxaphosphorinane, however, forms 2-amido-2-phenylimido-1,3,2-dioxaphosphorinanes (6) retaining the heterocyclic ring system. The latter are also obtained in the reaction of 2-dialkylamido-1,3,2-dioxaphosphorinanes with CCl4 and aniline. 2-Amino-2-oxo-1,3,2-dioxaphosphorinanes (8) are prepared from 2-hydrido-2-oxo-1,3,2-dioxaphosphorinane (7) by means of the Atherton-Todd reaction. In combination with the Staudinger reaction the latter yields N(2-oxo-1,3,2-dioxaphosphorinanyl)phosphazenes (10).
    Notes: 2-Alkoxy- und 2-Dialkylamido-1,3,2-dioxaphosphorinane reagieren mit CCl4 bei An- und Abwesenheit protischer Nucleophile unter Ringöffnung zu acyclischen Phosphorsäureesterderivaten. 2-Anilido-1,3,2-dioxaphosphorinan wird dagegen unter Erhalt des heterocyclischen Ringsystems in 2-Amido-2-phenylimido-1,3,2-dioxaphosphorinane (6) überführt. Letztere werden auch bei der Umsetzung von 2-Dialkylamido-1,3,2-dioxaphosphorinane mit CCl4 und Anilin erhalten. Aus 2-Hydrido-2-oxo-1,3,2-dioxaphosphorinan (7) sind mit Hilfe der Atherton-Todd-Reaktion 2-Amido-2-oxo-1,3,2-dioxaphosphorinane (8) und in Kombination mit der Staudinger-Reaktion N-(2-Oxo-1,3,2-dioxaphosphorinanyl)phosphazene (10) darstellbar.
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  • 2
    ISSN: 0044-2313
    Keywords: N-dichlorophosphanyl triphenylphosphazane ; N-phosphanyl, N-phosphinoyl phosphazenes ; 31P n.m.r. data ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Replacement and Oxidation Reactions of N-Dichlorophosphanyl Triphenylphosphazene, Ph3P=N—PCl2The title compound (1) reacts with MeOH, EtOH, PhOH, EtSH, and water forming N-phosphanyl or N-phosphinoyl phosphazenes, resp., Ph3P=N—PX2 (X = OPh(8), SEt(9)) or Ph3P=N—PH(O)X (X = Cl(3), OH(4), OMe(5), OEt(7)). The reaction of 1 with P(NEt2)3 yields Ph3P=N—P(NEt2)2 (10). Ph3P=N—PF2(11) and Ph3P=N—PH(O)F (12) are obtained by chlorine-fluorine exchange. The N-phosphanyl compounds 1, 8, 9 and 11 are oxidized by NO2 yielding the corresponding N-phosphoryl derivatives, Ph3P=N—P(O)X2 (X = Cl(2), OPh(13), SEt (14), F(15)). The thiophosphoryl compounds, (Ph3P=N—P(S)X2 (X = Cl(16), OPh(17), F(18)) are obtained by oxidizing 1, 8, and 11 with sulfur.
    Notes: Die Titelverbindung (1) reagiert mit den protischen Nucleophilen MeOH, EtOH, PhOH, EtSH und Wasser zu Phosphanyl- bzw. Phosphinoylphosphazenen, Ph3P=N—PX2 (X = OPh (8), SEt (9)) bzw. Ph3P=N—PH(O)X (X = Cl(3), OH(4), OMe(5), OEt(7)). Die Reaktion von 1 mit P(NEt2)3 ergibt Ph3P=N—P(NEt2)2 (10) und durch Chlor-Fluor-Austausch werden Ph3P=N—PF2 (11) und Ph3P=N—PH(O)F (12) erhalten. Die N-Phosphanylverbindungen 1, 8, 9 und 11 werden durch NO2 zu den entsprechenden N-Phosphorylderivaten Ph3P=N—P(O)X2 (X = Cl(2), OPh(13), SEt (14), F(15)) und die Verbindungen 1, 8 und 11 durch Schwefel zu Thiophosphorylverbindungen (Ph3P=N—P(S)X2(X = Cl(16), OPh(17), F(18)) oxydiert.
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  • 3
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Zeitschrift für anorganische Chemie 603 (1991), S. 145-150 
    ISSN: 0044-2313
    Keywords: Fluoro(organyl)phosphanes ; syntheses ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: A simple Synthesis of Fluoro(organyl)PhosphanesA simple synthesis of fluoro(organyl)phosphanes, RPF2, and R2PF, which is based on the reaction of the corresponding chloro compounds with triethylamine-HF adducts in the presence of free triethylamine, is presented. The method even allows the synthesis of compounds of extremely low stability.
    Notes: Es wird ein einfaches Verfahren zur Synthese von Organyldifluor-und Diorganylfluorphosphanen, RPF2 und R2PF, vorgestellt, das auf der Umsetzung der entsprechenden Chlorverbindungen mit Triethylamin-HF-Addukten in Gegenwart von freiem Triethylamin beruht und auch die Synthese sehr wenig stabiler Vertreter dieser Substanzklasse erlaubt.
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  • 4
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Zeitschrift für anorganische Chemie 620 (1994), S. 1099-1102 
    ISSN: 0044-2313
    Keywords: Trifluorohalomethanes ; Trifluoromethylphosphonium Halides ; Trifluoromethylphosphanes ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: On the Reaction of Trifluorohalomethanes with PhosphanesThe reactions of trifluorohalomethanes CF3X (X = Cl, Br, I) with Ph3P, Bu3P, (Me2N)3P, and (Et2N)3P were investigated. CClF3 does not react. In the reactions of CBrF3 and CF3I with Bu3P in acetonitrile trifluorophosphonium salts, [Bu3PCF3]X (X = Br, I), are formed, whereas gaseous CF3I and Bu3P yield Bu2PCF3. Depending on the reaction conditions the aminophosphanes form either [(R2N)3PX]X (R = Me, Et; X = Br, I) and CF3H or [(R2N)3PCF3]X.
    Notes: Es wird über die Reaktionen der Trifluorhalomethane CF3X (X = Cl, Br, I) mit Ph3P, Bu3P, (Me2N)3P und (Et2N)3P berichtet. CClF3 verhält sich inert. CBrF3 und CF3I bilden in Acetonitril mit Bu3P Trifluormethylphosphoniumsalze, [Bu3PCF3]X (X = Br, I), während sich gasförmiges CF3I mit Bu3P zu Bu2PCF3 umsetzt. Die Aminophosphane reagieren in Abhängigkeit von den Reaktionsbedingungen zu [(R2N)3PX]X (R = Me, Et; X = Br, I) und CF3H bzw. [(R2N)3PCF3]X.
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  • 5
    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.
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  • 6
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Zeitschrift für anorganische Chemie 405 (1974), S. 109-112 
    ISSN: 0044-2313
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Reaction of Imidodiphosphoryl Tetrachloride with Phosphorus PentachlorideImidodiphosphoryl tetrachloride quantitatively reacts with PCl5 to form, HCl, POCl3, and Cl3P=N—POCl2. The mechanism of the reaction is discussed. Using 32P-labeled PCl5 was proved that the attack of the PCl5 to imidodiphosphoryl tetrachloride does occur about an oxygen atom.
    Notes: Imidodiphosphoryltetrachlorid reagiert mit PCl5 quantitativ zu HCl, POCl3 und Cl3P=N—POCl2. Der mögliche Reaktionsmechanismus wird diskutiert. Mit 32P-markiertem PCl5 gelang der Nachweis, daß der Angriff des PCl5 am Imidodiphosphoryltetrachlorid über ein Sauerstoffatom erfolgt.
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  • 7
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Zeitschrift für anorganische Chemie 404 (1974), S. 219-224 
    ISSN: 0044-2313
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Preparation and Properties of Imidodiphosphoric Acid AmidesTrichlorophosphazene phosphoryldichloride, Cl3P=N—P(O)Cl2, reacts with the stoichiometric amount of anhydrous formic acid resulting the tetrachloride of the imidodiphosphoric acid, Cl2(O)P—NH—P(O)Cl2. This tetrachloride yields with diazomethane the N-methyl compound, Cl2(O)P—N(CH3)—P(O)Cl2. The tetramide of the imidodiphosphoric acid and its octalkyl derivatives are obtained by reaction of the tetrachloride with ammonia, dimethylamine, and diethylamine, respectively.
    Notes: Trichlorphazenphosphoryldichlorid, Cl3P=N—P(O)Cl2, reagiert mit der stöchiometrischen Menge wasserfreier Ameisensäure zum Imidodiphosphorsäuretetrachlorid, Cl2(O)P—NH—P(O)Cl2. Mit Diazomethan bildet dieses das N-Methylderivat, Cl2(O)P—N(CH3)—P(O)Cl2. Durch Umsetzung mit Ammoniak, Dimethyl- bzw. Diäthylamin werden das Imidodiphosphorsäuretetramid sowie die entsprechenden Octaalkylderivate erhalten.
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  • 8
    ISSN: 0044-2313
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Direct Synthesis of Trialk(ar)yl Phosphites and Trialk(ar)yl Trithiophosphites from Elemental PhosphorusIn the presence of triethylamine trialk(ar)yl phosphites, P(OR)3, and trialk(ar)yl trithiophosphites, P(SR)3, (R = alk, ar) can be produced in good yields by treating elemental phosphorus, P4, with CCl4 and alcohols or thiols, resp., in dipolar-aprotic solvents. Whereas. Whereas in the reaction with alcohols the P4 degradation happens according to scheme 1, the reaction with thiols occurs via the intermediate formation of disulfanes, R2S2, which then react with P4 forming the trithiophosphites (eqs. (6) and (7)).
    Notes: In dipolar-aprotischen Lösungsmitteln lassen sich Trialk(ar)ylphosphite und -trithiophosphite, P(OR)3 bzw. P(SR)3 (R = Alk, Ar), in guten Ausbeuten durch die Umsetzung von P4 mit CCl4 und Alkoholen bzw. Thiolen in Gegenwart von Triethylamin herstellen. Während der P4-Abbau in der Reaktion mit den Alkoholen entsprechend Schema 1 erfolgt, verläuft die Reaktion mit den Thiolen über die intermediäre Bildung von Disulfanen, R2S2, die ihrerseits mit P4 zu den Trithiophosphiten reagieren (Gl. (6) und (7)).
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  • 9
    ISSN: 0044-2313
    Keywords: Organylfluorophosphanes ; reaction mechanism ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: The Dimerization of Di(n-butyl)fluorophosphane and its Reaction with BenzaldehydeThe phosphorus atom of organylfluorophosphanes possesses electrophilic as well as nucleophilic properties. This dualistic character decisively determines both their disproportionation and their reaction with aldehydes. The phoshanylphoshorane n-Bu2P—PF2(n-Bu)2, 1 b, has been proved to be the intermediat product of the disproportionation of n-Bu2PF. In the presence of an equimolar amount of Et3N an equilibrium exists between 1 b and the monomeric n-Bu2PF. n-Bu2PF react with benzaldehyde forming the phosphinitophoshorane n-Bu2P′—O—CHPh—PF2(n-Bu)2, 3 a. Reliable information on the reaction pathway has been obtained by means of crossing experiments.
    Notes: In Organylfluorphosphanen besitzt das Phosphoratom sowohl elektrophile als auch nucleophile Eigenschaften. Dieser dualistische Charakter ist für die Disproportionierung von Diorganylfluorphosphanen, R2PF, und für ihre Reaktion mit Aldehyden von entscheidender Bedeutung. Bei der Disproportionierung von n-Bu2PF tritt das Phosphanylphosphoran n-Bu2P—PF2(n-Bu)2, 1b, als Zwischenprodukt auf. In Gegenwart von äquimolaren Mengen Et3N steht 1 b mit dem monomeren n-Bu2PF im Gleichgewicht. n-Bu2PF reagiert mit Benzaldehyd zum Phosphinitophosphoran n-Bu2P′—O—CHPh—PF2(n-Bu)2, 3 a, dessen Bildungsweg durch „Kreuzungsexperimente“ eindeutig ermittelt werden konnte.
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  • 10
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Zeitschrift für anorganische Chemie 617 (1992), S. 148-154 
    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.
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