Synthesis of StableN′,N′,N′′,N′′-Tetramethylguanidine-Substituted σ4(P)- and σ3(P)-Organophosphorus Compounds withN-Protonated P–N Bonds - The First σ3-Phosphorus-Substituted Ammonium Salts⋆

Plack, Volker; Münchenberg, Jochen; Thönnessen, Holger; Jones, Peter G.; Schmutzler, Reinhard

doi:10.1002/(sici)1099-0682(199806)1998:6<865::aid-ejic865>3.0.co;2-i

Cited by 16 publications

(13 citation statements)

References 25 publications

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“…The use of the tetramethylguanidine substituent at phosphorus [4] furnished the first a'X'-phosphorus-containing ammonium salts; the stability of 8 was sufficient to permit a single X-ray structure determination [5].…”

Section: Please Scroll Down For Articlementioning

confidence: 99%

The Triphenylmethyl Group- a Kinetically Stabilizing Substituent and Protecting Group in Organophosphorus Chemistry

Plack

Schmutzler

1999

Phosphorus, Sulfur, and Silicon and the Related Elements

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Section: Please Scroll Down For Articlementioning

confidence: 99%

The Triphenylmethyl Group- a Kinetically Stabilizing Substituent and Protecting Group in Organophosphorus Chemistry

Plack

Schmutzler

1999

Phosphorus, Sulfur, and Silicon and the Related Elements

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“…Die von uns untersuchte Klasse der [N-(N',N', N",N"-tetramethyl)guanidinyl]-substituierten Phosphor(III)-Verbindungen (TMG-Derivate) [9,10] weist eine Reihe möglicher Protonierungszentren auf. Es wurden, abhängig von der Nucleophilie des 0932-0776/99/0600-0761 $ 06.00 © 1999 Verlag der Zeitschrift für Naturforschung, Tübingen • www.znaturforsch.com K CalixO® + H3 N®R' D Schema 1.…”

Section: Introductionunclassified

“…Phosphoratoms, sowohl die Protonierung des Phos phoratoms als auch die des Iminostickstoffatoms beobachtet [10]. Bisher sind keine TMG-substituierten Phosphoniumsalze mit Oxoanionen beschrie ben worden.…”

Section: Introductionunclassified

“…Die Umsetzung des erhaltenen Phosphoniumsalzes mit einem weiteren Äquivalent Säure führt zur Protonierung eines Iminostickstoffatoms. Durch die so veränderten elektronischen Ei genschaften des Kations wird die zweite unprotonierte TMG-Gruppierung zum elektrophilen Zen trum, so daß eine Umlagerung von III zur bikationischen <r3(P)-Verbindung IV eintritt[10].Die Reaktion der p-r<?rr-Butylcalix[4]aren-Derivate 1 und 2 mit rm -Butylbis[N -(N ',N ',N",N"-tetramethyl)guanidinyl]phosphin 3 führt zur Salzbil dung (siehe Schema 3). In beiden Fällen konnte die…”

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Synthese und Röntgenstrukturanalyse der ersten terf-Butylcalix[4]arensalze mit einem Phosphonium-Kation / Synthesis and X-Ray Structure Analysis of the First rm-Butylcalix[4]arene Salts with a Phosphonium Cation

Siedentop

Neda

Thönnessen

et al. 1999

Zeitschrift Für Naturforschung B

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Sonderdruckanforderungen an R. Schmutzler. Fax: +49 531 391 5387. E-mail: r.schmutzler@tu-bs.de Z. Naturforsch. 54 b, 7 6 1 -7 6 6 (1999); eingegangen am 11. Februar 1999 terr-Butylcalix[4]arene A nions, rm -Butylcalix[4]arenes (Phosphorus-Substituted), Phospho nium Salts (Tetramethylguanidine-Substituted), X-Ray DataThe reactions o f ter/-butylcalix[4]arene (1) and the phosphorus-substituted rm -butylcalix-[4]arene (2), respectively, with terf-butylbis[N-(N',N',N",N"-tetramethyl)guanidinyl]phosphine (3) led to the first calix[4]arene-anions with the protonated phosphonium cations 4 and 5. N o protonation o f the imino nitrogen atom was observed.In the case o f compound 4, a single crystal X-ray structure analysis has been conducted. In compound 5, phosphorus atoms in the oxidation states +III and +V are present in one molecule.

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“…Due to the stability of the triphenylmethyl anion, the P±C-bond in triphenylmethylsubstituted phosphorus compounds is frequently unstable under strongly basic or strongly reducing conditions, e. g. in the presence of tetramethylguanidine [3], organolithium reagents [4], triphenylmethyl sodium [5], or alkali metals [6]. Nevertheless, in all these cases the cleavage of the P±C-bond led only to nonselective decomposition of the compounds employed.…”

Section: Introductionmentioning

confidence: 99%

Selective P-C-Bond Cleavage in P(III)-Triphenylmethyl Compounds

Plack¹,

Goerlich²,

Schmutzler³

1998

Z. anorg. allg. Chem.

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Synthesis of StableN′,N′,N′′,N′′-Tetramethylguanidine-Substituted σ4(P)- and σ3(P)-Organophosphorus Compounds withN-Protonated P–N Bonds - The First σ3-Phosphorus-Substituted Ammonium Salts⋆

Cited by 16 publications

References 25 publications

The Triphenylmethyl Group- a Kinetically Stabilizing Substituent and Protecting Group in Organophosphorus Chemistry

The Triphenylmethyl Group- a Kinetically Stabilizing Substituent and Protecting Group in Organophosphorus Chemistry

Synthese und Röntgenstrukturanalyse der ersten terf-Butylcalix[4]arensalze mit einem Phosphonium-Kation / Synthesis and X-Ray Structure Analysis of the First rm-Butylcalix[4]arene Salts with a Phosphonium Cation

Selective P-C-Bond Cleavage in P(III)-Triphenylmethyl Compounds

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