Synthesis and characterization of some organo-all-tin dendrimers with different peripheral substituents

Schumann, Herbert; Aksu, Yılmaz; Wassermann, Birgit C.

doi:10.1016/j.jorganchem.2005.11.012

Cited by 13 publications

(10 citation statements)

References 41 publications

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“…Schuman and workers were able to form the Grignard salt, FpMgBr, from Fp 2 dimer, 1,2-dibromoethane, and magnesium turnings in THF solution within 5 h at room temperature [56]. It should be mentioned that the research group of Maslennikov was able to form a Grignard salt of the type FpMgCl from FpCl instead of directly from the Fp 2 dimer.…”

Section: Synthesis Of the ( 5 -C 5 H 5 )(Co) 2 Fe Metalatementioning

confidence: 99%

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Recent chemistry of the η5-cyclopentadienyl dicarbonyl iron anion

Theys

Dudley

Hossain

2009

Coordination Chemistry Reviews

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Section: Synthesis Of the ( 5 -C 5 H 5 )(Co) 2 Fe Metalatementioning

confidence: 99%

“…Continuing their study of metallodendrimers, Schumann and coworkers prepared [56] several Fp dendrimers. One of the dendrimers studied had four peripheral Fp moieties after substitution of the four chloro groups (Scheme 110).…”

Section: Fe-ge Fe-sn and Fe-pb Bond Formation (Table 8)mentioning

confidence: 99%

Recent chemistry of the η5-cyclopentadienyl dicarbonyl iron anion

Theys

Dudley

Hossain

2009

Coordination Chemistry Reviews

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“…21 The hydrostannylation of tetravinyl-and tetraallylstannane with Ph 3 SnH runs in a similar way. 15 In contrast to the results described above and again in analogy with our earlier investigations on corresponding hydrostannylation reactions, 16 tetra(but-3-enyl)stannane reacts with triphenylgermane in the presence of 5 mol % of AIBN, yielding tetrakis[4-(triphenylgermyl)butyl]stannane (4) (Scheme 2). The pure white solid obtained in almost quatitative yields is soluble in all commonly used organic solvents except alkanes and diethyl ether.…”

Section: Resultsmentioning

confidence: 55%

“…Recently, we succeeded in the sythesis of the tin analogues of the organosilicon 7e, and organogermanium 8c,d,g,h dendrimers already known. In the meantime, we developed a method to synthesize the first all -tin dendrimer by the divergent as well as by the convergent route and consequently prepared a series of novel tin-based dendrimers . In this paper we describe a simple method for the synthesis of hybrid metallodendrimers of group 14 elements, resulting in the isolation of the first Si/Ge/Sn heterotrimetallic dendrimer.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Silicon-Based Group 14 Dendrimers Si{(CH₂)₂Sn[(CH₂)₄MPh₃]₃}₄ (M = Ge, Sn)

Schumann

Aksu

2006

Organometallics

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The catalytic hydrogermylation of Si(CHCH2)4 with Ph3GeH yielded Si(CH2CH2GePh3)4 (1). In contrast, Sn(CHCH2)4 and Sn(CH2CHCH2)4 reacted with Ph3GeH under the same conditions, forming Ph3Ge(CH2)2GePh3 (2) and Ph3Ge(CH2)3GePh3 (3), respectively, whereas the reaction of Sn(CH2CH2CHCH2)4 and Ph3GeH afforded the expected tin-based metallodendrimer Sn[(CH2)4GePh3]4 (4). The reactions of Si[(CH2)2SnBr3]4 with the Grignard reagents RMgBr (R = CHCH2, CH2CHCH2, (CH2)2CHCH2)) produced Si[(CH2)2Sn(CHCH2)3]4 (5), Si[(CH2)2Sn(CH2CHCH2)3]4 (6), and Si[(CH2)2Sn(CH2CH2CHCH2)3]4 (7). While hydrogermylation of 5 and 6 with Ph3GeH resulted in the formation of 2 and 3, respectively, compound 7 reacted with Ph3GeH, providing the expected second-generation Si/Ge/Sn heterometallodendrimer Si{(CH2)2Sn[(CH2)4GePh3]3}4 (8). Correspondingly, hydrostannylation of 7 with Ph3SnH yielded Si{(CH2)2Sn[(CH2)4SnPh3]3}4 (9). All compounds were characterized by multinuclear NMR studies (1H, 13C, 119Sn), mass spectrometry (MALDI-TOF, EI), and elemental analyses.

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“…In consideration of our earlier results, 26,27,29 demonstrating that hydrostannylation of vinyl and allyl tin compounds is accompanied by unwanted redistribution reactions, we chose 1,4-bis(tribut-3-enylstannyl)butane and 1,5-bis(tribut-3-enylstannyl)pentane as starting materials. Scheme 1.…”

Section: Main Group Metal Compoundsmentioning

confidence: 99%

Synthesis and characterization of α, ω‐bis [tri ‐ (w ‐ triphenylstannyl) butylstannyl] alkanes as starting materials for organotin dendrimers

Aksu¹,

Aksu²,

Schumann³

2007

Applied Organom Chemis

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Sn[(CH 2 ) 4 SnPh 2 (CH 2 ) 3 OH] 3 (9a, b). All compounds were characterized by multinuclear NMR studies( 1 H, 13 C, 119 Sn), mass spectrometry (MALDI-TOF, EI) and elemental analyses. Contract/grant sponsor: Fonds der Chemischen Industrie, Schering A.G.. to the peripheral tin atoms in the second-generation tincentered dendrimers Sn{(CH 2 ) n Sn[(CH 2 ) 4 SnPh 3 ] 3 } 4 (n = 3, 4) resulted in the formation of mixtures of different incompletely substituted and inseparable compounds. 27 Third-generation tin-centered dendrimers are not available by this route.Another possibility to get dendrimers containing a high percentage of tin is to start with alkyl-bridged ditin hexaalkenides (C n H 2n−1 ) 3 Sn(CH 2 ) m Sn(C n H 2n−1 ) 3 as a core. Distannylated alkyl compounds including compounds with short alkyl spacers have been known since 1930 31 and compounds containing aromatic spacers have been known since as early as 1925. 32 Recently, Dakternieks and coworkers 33 and Jousseaume et al. 34 investigated α,ω-ditin hexaalkenides and arylides as starting compounds for new materials. Here we describe the synthesis and characterization of two new α, ω-bis [tri -(w -triphenylstannyl) butylstannyl] alkanes and some of their derivatives as starting materials for organotin dendrimers. Main Group Metal Compoundssubstituents accessible for further reactions to build up second-generation dendrimers with a high tin content. In consideration of our earlier results, 26,27,29 demonstrating that hydrostannylation of vinyl and allyl tin compounds is accompanied by unwanted redistribution reactions, we chose 1,4-bis(tribut-3-enylstannyl)butane and 1,5-bis(tribut-3-enylstannyl)pentane as starting materials. Scheme 1. Synthesis of compounds 4a, b. Scheme 2. Synthesis of compounds 5a, b. Main Group Metal Compounds α,ω-bis [tri -(w -triphenylstannyl) butylstannyl] alkanes 523 Scheme 3. Synthesis of compounds 6a, b.Figure 1. 119 Sn{ 1 H}NMR spectra of compounds 6a and 6b in CDCl 3 .Figure 2. MALDI-TOF mass spectra of 6a and 6b. Scheme 4. Synthesis of compounds 7a, b, 8a, b and 9a, b.These first-generation dendrimers 6a, b, 7a, b, 8a, b, and 9a, b could not be crystallized, thus excluding X-ray structural determination. However, the purity and the correctness of the proposed structures of the compounds were proved by their NMR and MALDI-TOF spectra. They are potential starting materials for the synthesis of dendrimers of the second generation. Further work in this area is in progress. EXPERIMENTAL GeneralAll manipulations involving air-sensitive compounds were carried out in dry, oxygen-free solvents under an inert atmosphere of nitrogen using standard Schlenk techniques. Melting points were measured in sealed capillaries with

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Synthesis and characterization of some organo-all-tin dendrimers with different peripheral substituents

Cited by 13 publications

References 41 publications

Recent chemistry of the η5-cyclopentadienyl dicarbonyl iron anion

Recent chemistry of the η5-cyclopentadienyl dicarbonyl iron anion

Synthesis and Characterization of Silicon-Based Group 14 Dendrimers Si{(CH₂)₂Sn[(CH₂)₄MPh₃]₃}₄ (M = Ge, Sn)

Synthesis and characterization of α, ω‐bis [tri ‐ (w ‐ triphenylstannyl) butylstannyl] alkanes as starting materials for organotin dendrimers

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Synthesis and characterization of some organo-all-tin dendrimers with different peripheral substituents

Cited by 13 publications

References 41 publications

Recent chemistry of the η5-cyclopentadienyl dicarbonyl iron anion

Recent chemistry of the η5-cyclopentadienyl dicarbonyl iron anion

Synthesis and Characterization of Silicon-Based Group 14 Dendrimers Si{(CH2)2Sn[(CH2)4MPh3]3}4 (M = Ge, Sn)

Synthesis and characterization of α, ω‐bis [tri ‐ (w ‐ triphenylstannyl) butylstannyl] alkanes as starting materials for organotin dendrimers

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Synthesis and Characterization of Silicon-Based Group 14 Dendrimers Si{(CH₂)₂Sn[(CH₂)₄MPh₃]₃}₄ (M = Ge, Sn)