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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: 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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  • 2
    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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