Phosphoraustausch im Cyclophosphazenring bei der Reaktion Hydridocyclotri(phosphazen)/Perthiophosphonsäureanhydrid [1] / Exchange of Phosphorus in the Cyclophosphazene Ring in the Reaction Hydridocyclotri (phosphazene )/Perthiophosphonic Anhydride [1]

Högel, Johann; Schmidpeter, Alfred

doi:10.1515/znb-1979-0706

Cited by 6 publications

References 4 publications

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N-Thiophosphorylated andN-Phosphorylated Iminophosphoranes [R3P=N–P(X)R′2; × = O, S] as Models for Dendrimers: Synthesis, Reactivity and Crystal Structures

Larré

Donnadieu

Caminade

et al. 1999

Eur. J. Inorg. Chem.

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Several R3P=N–P(X)R′2 and Fe[C5H4Ph2P=N–P(X)R′2]2 derivatives (X = S, O) are readily obtained from Staudinger reactions between phosphanes and N3–P(X)R′2. The P=N–P=X groups are easily alkylated on the × atom with methyl or isopropyl triflates. The alkylation induces a lengthening of the P–X bond, as shown by X‐ray diffraction studies. This corresponds to a weakening of the P–X bond which can be cleaved with P(NMe2)3 to yield [P=N–P:] linkages. The presence of tricoordinated phosphorus atoms opens the way to a versatile reactivity, including the reaction with alkyl iodides and functionalized azides. These molecules are good models for screening which types of reagents and reactions could be used with macromolecules possessing also P=N–P=X linkages, such as dendrimers.

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N-Thiophosphorylated andN-Phosphorylated Iminophosphoranes [R3P=N–P(X)R′2; × = O, S] as Models for Dendrimers: Synthesis, Reactivity and Crystal Structures

Larré

Donnadieu

Caminade

et al. 1999

Eur. J. Inorg. Chem.

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Four‐Membered Sulfur Heterocycles

Dittmer

Sedergran

1985

Chemistry of Heterocyclic Compounds: A Series of Monographs

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Vier‐ und fünfgliedrige Phosphorheterocyclen, 36 ¹⁾ 1,3‐Dipolare Cycloadditionen an Azaphosphole und Azaphospholine

Schmidpeter

Criegern

1979

Chem. Ber.

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and azaphospholines (4), give stable [3 + 21-cycloadducts (3, 5, 8, 9, 11) with arylnitrile oxides, diphenylnitrile imine, and nitrones which can be isolated in crystalline form. The bridgehead position in the bicyclooctane structure of the adducts favours phosphorus pentacoordination and thus enhances adduct stability; NMR spectroscopic results agree to the meridional arrangement of the bicyclus. The cycloaddition to azaphospholes depends on the 1,3-dipoles in an order known from other dipolarophiles and decreases with the phosphorus substituents Me > Ph > NMe,. The adducts of the 3,4-dihydroisoquinoline N-oxide (11 f, g) dissociate reversibly in solution.1,3-Dipolare Cycloadditionen a n Phosphanmethylene und Phosphanimide wurden wiederholt untersucht. Jedoch liefern nur die ersteren in gunstigen Fallen mit Nitriloxiden '3 3, und Nitronen 4, tatsachlich Cycloaddukte mit pentakoordiniertem Phosphor. Phosphanimide reagieren damit entweder iiberhaupt nicht oder ergeben, offenbar iiber die Cycloadditionsstufe hinweg, Phosphanoxide als deren Zerfallsprodukt 5 , (1).Nitrilimine addieren sich entweder gar nicht oder, wenn die auftretenden Ladungen stabilisiert werden konnen, lediglich zum Betain ').Phosphanimide, in denen die Phosphazengruppe Teil eines Funfrings ist, zeigen gegeniiber dem acyclischen Normalfall bei [2 + 21-Cycloadditionen eine gesteigerte Reaktivitat und hohere Adduktstabilitat 'I. Sie ist auf die Begiinstigung der Phosphorpentakoordi-

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Phosphoraustausch im Cyclophosphazenring bei der Reaktion Hydridocyclotri(phosphazen)/Perthiophosphonsäureanhydrid [1] / Exchange of Phosphorus in the Cyclophosphazene Ring in the Reaction Hydridocyclotri (phosphazene )/Perthiophosphonic Anhydride [1]

Cited by 6 publications

References 4 publications

N-Thiophosphorylated andN-Phosphorylated Iminophosphoranes [R3P=N–P(X)R′2; × = O, S] as Models for Dendrimers: Synthesis, Reactivity and Crystal Structures

N-Thiophosphorylated andN-Phosphorylated Iminophosphoranes [R3P=N–P(X)R′2; × = O, S] as Models for Dendrimers: Synthesis, Reactivity and Crystal Structures

Four‐Membered Sulfur Heterocycles

Vier‐ und fünfgliedrige Phosphorheterocyclen, 36 ¹⁾ 1,3‐Dipolare Cycloadditionen an Azaphosphole und Azaphospholine

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Phosphoraustausch im Cyclophosphazenring bei der Reaktion Hydridocyclotri(phosphazen)/Perthiophosphonsäureanhydrid [1] / Exchange of Phosphorus in the Cyclophosphazene Ring in the Reaction Hydridocyclotri (phosphazene )/Perthiophosphonic Anhydride [1]

Cited by 6 publications

References 4 publications

N-Thiophosphorylated andN-Phosphorylated Iminophosphoranes [R3P=N–P(X)R′2; × = O, S] as Models for Dendrimers: Synthesis, Reactivity and Crystal Structures

N-Thiophosphorylated andN-Phosphorylated Iminophosphoranes [R3P=N–P(X)R′2; × = O, S] as Models for Dendrimers: Synthesis, Reactivity and Crystal Structures

Four‐Membered Sulfur Heterocycles

Vier‐ und fünfgliedrige Phosphorheterocyclen, 36 1) 1,3‐Dipolare Cycloadditionen an Azaphosphole und Azaphospholine

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Vier‐ und fünfgliedrige Phosphorheterocyclen, 36 ¹⁾ 1,3‐Dipolare Cycloadditionen an Azaphosphole und Azaphospholine