Phosphororganische Verbindungen, XIX. Reduktion von Phosphorverbindungen mit Alkalimetallen

Horner, L.; Beck, P.; Hoffmann, Hartmut

doi:10.1002/cber.19590920920

Cited by 87 publications

(33 citation statements)

References 24 publications

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“…The blue color of the solution disappeared in a few minutes after the addition of the last drop of phosphorus electrophile. The reaction was quenched by solid NH 4 Cl, and, after removal of the solvents, the products were isolated by radial chromatography (or by distillation). The results of this set of experiments are presented in Table 1 (runs 7-11).…”

Section: Methodsmentioning

confidence: 99%

“…The solvent was removed in vacuum and the products were separated by radial chromatography. The reduction products were eluted with CHCl 3 ( 4 Cl was added and the ammonia was evaporated at 10 mm Hg. The products were distilled (Table 2; runs 12 and 13) or poured into the mixture of toluene and aqueous KHSO 4 solution.…”

Section: Methodsmentioning

confidence: 99%

“…Then 1.5 g of NH 4 Cl was added and the ammonia was evaporated at 10 mm Hg. The residue was poured into a mixture of toluene and aqueous KHSO 4 solution.…”

Section: Methodsmentioning

confidence: 99%

“…On the other hand, Horner [4] was able to demonstrate that a phosphane sulfide can be reduced easily with sodium to the corresponding phosphane. Also, Issleib [5] reported that treatment of diphosphane disulfide with sodium in dioxan furnished the corresponding diphosphane or sodium phosphinide, depending on the structures of the starting materials and the conditions of the reaction.…”

Section: P(y) CL [Y: O S]mentioning

confidence: 96%

“…• C. The reaction mixture was stirred for 30 min, and then 0.45 g of NH 4 Cl was added. Ammonia was removed in vacuum and the residue was distilled; t-butylphenylphosphane (Kugelrohr, 60-61…”

Section: Reduction Of the Lithium T-butylphenylthiophosphane Sulphidementioning

confidence: 99%

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Reductive cleavage of the halogen–phosphorus and sulfur–phosphorus bonds with alkali metals

Stankiewicz

Nycz

Rachoń

2002

Heteroatom Chemistry

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

“…Then 1.5 g of NH 4 Cl was added and the ammonia was evaporated at 10 mm Hg. The residue was poured into a mixture of toluene and aqueous KHSO 4 solution.…”

Section: Methodsmentioning

confidence: 99%

Section: P(y) CL [Y: O S]mentioning

confidence: 96%

Section: Reduction Of the Lithium T-butylphenylthiophosphane Sulphidementioning

confidence: 99%

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Reductive cleavage of the halogen–phosphorus and sulfur–phosphorus bonds with alkali metals

Stankiewicz

Nycz

Rachoń

2002

Heteroatom Chemistry

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Diphosphapodanden,[12]-,[15]- und[18]Diphosphacoronanden, Diphosphacryptand-8 und Alkalimetall-Komplexe

Märkl

Reisinger

Kreitmeier

et al. 2002

HCA

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zum 90. Geburtstag gewidmet Diphosphapodands, [12]-, [15]-, and [18]Diphosphacoronands, Diphosphacryptand-8, and Alkali-Metal ComplexesThe cyclizing bis-phosphonium-salt formation of the open-chain bis-phosphine 17a (1,1,7,7-tetrabenzylhP.O.Ppodand-7i) with diethylene glycol derived dibromide 13a yields the 12-membered cyclic bis-phosphonium salt 20 (4,4,10,10-tetrabenzyl-12hO.P.O.P-coronand-4i-4,10-diium dibromide) in yields as high as 50 ± 60%. The 1,1,10,10-tetrabenzylhP.O 2 .P-podand-10i 17b forms with 13a the 15-membered cyclic bis-phosphonium salt 21 (7,7,13,13-tetrabenzyl-15hO 2 .P.O.P-coronand-5i-7,13-diium dibromide) with the same high yield. By quaternization of the bis-phosphine 17b with triethylene glycol derived dibromide 13b, the 18-membered 7,7,16,16-tetrabenzyl-18hO 2 .P.O 2 .P-coronand-6i-7,16-diium dibromide 24 is obtained in 50% yield, too. The Wittig reaction of the cyclic phosphonium salts with benzaldehyde yields the 12-, 15-, and 18-membered cyclic bisbenzylphosphine dioxides 9, 10, and 11 as cis-and trans-isomers beside trans-stilbene. The 7,13-dioxido-7,13-dibenzyl-15hO 2 .P.O 2 .P-coronand-5i 10 forms a crystalline 1 : 1 Na-complex 23, which exists as a dimer. The structure of 23 was established by an X-ray analysis and spectroscopic data. The 7,16-dibenzyl-18hO 2 .P.O 2 .Pcoronand-6i 28 that is available by reduction of 11 with CeCl 3 /LiAlH 4 reacts with triethylene glycol derived dibromide 13b under RugglyÀZiegler-dilution conditions to give the bicyclic bis-phosphonium salt 29 (1,10-Helvetica Chimica Acta ± Vol. 85 (2002) 1714 1 ) Bei Makrocyclen mit mehreren, insbesondere unterschiedlichen Heteroatomen im Ring f¸hrt die IUPACNomenklatur h‰ufig zu schwer nachvollziehbaren Bezeichnungen. F¸r makrocyclische Polyether hat Pederson [2] deshalb die Kronenether-Nomenklatur als Trivialnomenklatur eingef¸hrt. Bei verschiedenen Ringheteroatomen ebenso wie bei anellierten Ringsystemen ist die Pederson-Nomenklatur ebenfalls nicht mehr eindeutig. Die hier benutzte Coronanden-und Podanden-Nomenklatur wurde von Vˆgtle [5] eingef¸hrt. Hiernach werden offenkettige Systeme mit mehreren Donoratomen, die ebenfalls zur Komplexbildung geeignet sind, als Podanden und monocyclische Systeme mit Donoratomen (z.B. N, S, O) als Coronanden bezeichnet (die Bezeichnung Kronenether ist auf Coronanden beschr‰nkt, die ausschliesslich O-Atome als Donor-Atome besitzen. Sich von den Coronanden ableitende bicyclische Systeme werden als Cryptanden bezeichnet (siehe z.B. 2) [5]. dibenzylhP[O 2 ] 3 .P-cryptand-8i-1,10-diium dibromide) in 18% yield. Again, by the Wittig procedure with benzaldehyde, the 7,16-dioxidohP[O 2 ] 3 P-cryptand-8i 12 is obtained as the first diphosphacryptand. The FD-MS (CH 2 Cl 2 ) of the cyclic bis-phosphine dioxides 10 ± 12 show that they exist as [2M Na] complexes. The complex formation constants K a of 9 ± 11 with alkali-metal cations are studied and compared with the complex formation of corresponding crown ethers.

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Diphenylphosphine

Bianco¹,

Doronzo²,

Chan³

et al. 1976

Inorganic Syntheses

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Phosphororganische Verbindungen, XIX. Reduktion von Phosphorverbindungen mit Alkalimetallen

Cited by 87 publications

References 24 publications

Reductive cleavage of the halogen–phosphorus and sulfur–phosphorus bonds with alkali metals

Reductive cleavage of the halogen–phosphorus and sulfur–phosphorus bonds with alkali metals

Diphosphapodanden,[12]-,[15]- und[18]Diphosphacoronanden, Diphosphacryptand-8 und Alkalimetall-Komplexe

Diphenylphosphine

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