Organoboration of 3-(Trinethylstannayal)-2-Propyny-1-Ethers

Wrackmeyer, Bernd; Guldner, Gudrun; Abu‐Orabi, Sultan T.

doi:10.1016/0040-4020(89)80021-3

Cited by 18 publications

(5 citation statements)

References 30 publications

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“…However, the NMR spectra ( 1 H, 13 C, 29 Si NMR) of the silanes 1 and 2 did not change in the presence of BEt 3 (7), and the same is true for the germanes 3 and 4 ( 1 H, 13 C NMR). In the 11 B NMR spectra of these mixtures, the 11 B NMR signal is exactly in the position for free BEt 3 in C 6 D 6 (δ 11 B 85.5 ppm); this indicates negligible N-B donor-acceptor interactions between the silanes or germanes and BEt 3 .…”

Section: Proposed Mechanism Of the 11-organoborationsupporting

confidence: 49%

“…In the cases of aminoethynyl-Group-14 derivatives, it is tempting to assume that the reaction with trialkylboranes starts with the formation of an amine-borane adduct, especially in the diethylamino derivatives 1-5. However, the NMR spectra ( 1 H, 13 C, 29 Si NMR) of the silanes 1 and 2 did not change in the presence of BEt 3 (7), and the same is true for the germanes 3 and 4 ( 1 H, 13 C NMR). In the 11 B NMR spectra of these mixtures, the 11 B NMR signal is exactly in the position for free BEt 3 in C 6 D 6 (δ 11 B 85.5 ppm); this indicates negligible N-B donor-acceptor interactions between the silanes or germanes and BEt 3 .…”

Section: Proposed Mechanism Of the 11-organoborationmentioning

confidence: 66%

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Aminoethynyl‐silanes, ‐germanes and ‐stannanes: novel organometallic‐substituted enamines via 1,1‐organoboration

Wrackmeyer

Tok

Guldner

et al. 2003

Applied Organom Chemis

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The reactions of diethylaminoethynyl(trimethyl)silane (1), bis(diethylaminoethynyl)methylsilane (2), diethylaminoethynyl(trimethyl)germane (3), dimethylaminoethynyl(triethyl)germane (4), diethylaminoethynyl(trimethyl)stannane (5) and methyl(phenyl)aminoethynyl(trimethyl)stannane (6) with trialkylboranes [BEt 3 (7b), BPr 3 (7c), B i Pr 3 (7d) and 9-alkyl-9-borabicyclo[3.3.1]nonanes 9-Me-9-BBN (8a) and 9-Et-9-BBN (8b)] were studied. The alkynes 1 and 2 did not react even with boiling BEt 3 , whereas the reactions of 3-6 afforded mainly novel enamines [(E)-1-amino-1-trialkylgermyl- -1-trimethylstannyl-2-dialkylboryl-alkenes (13, 14)]. This particular stereochemistry is unusual for products from 1,1-organoboration reactions, indicating a special influence of the amino group. The starting materials and products were characterized by multinuclear magnetic resonance spectroscopy ( 1 H, 11 B, 13 C, 15 N, 29 Si, 119 Sn NMR). 2-dialkylboryl-alkenes (9, 10), (E)-1-diethylamino-1-trimethylstannyl-2-dialkylboryl-alkenes (11, 12), (E)-1-methyl(phenyl)amino

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Section: Proposed Mechanism Of the 11-organoborationsupporting

confidence: 49%

Section: Proposed Mechanism Of the 11-organoborationmentioning

confidence: 66%

Aminoethynyl‐silanes, ‐germanes and ‐stannanes: novel organometallic‐substituted enamines via 1,1‐organoboration

Wrackmeyer

Tok

Guldner

et al. 2003

Applied Organom Chemis

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“…However, the formation of 4 was accompanied by rearrangement to 5 (Scheme 2d) which was complete after 72 h at room temperature. Analogous rearrangements have been reported in the cases of 2,5-dihydro-1,2-oxoniaboratoles [7] or 2,5-dihydro-1,2,5-oxoniasila-boratoles [8], Compound 5 could be distilled without decomposition. In contrast, no reaction was observed between 1 and trimethylsilyl-bis(trimethylstannyl)amine, Me 3 SiN(SnMe 3 ) 3 (Scheme 1e).…”

Section: Synthesis Of the 25-dihydro-1-azonia-2-stanna-5-boratolesmentioning

confidence: 89%

Novel Organo-Substituted 2,5-Dihydro-1-Azoniaand -1-Phosphonia-2-Stanna-5-Boratoles

Wrackmeyer¹,

Kerschl²,

Maisel³

1998

Main Group Metal Chemistry

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E)-2-(chlorodimethylstannyl)-3-diethylboryl-pent-2-ene 1 reacts with methylbis(trimethylstannyl)amine and tris(trimethylstannyl)amine to give the new 2,5-dihydro-1-azonia-2-stanna-5-boratoles 3 and 4, respectively, of which 4 rearranges irreversibly into the 1-aza-2-stanna-5-bora-cyclopentane derivative 5. The reaction of 1 with lithium bis(trimethylsilyl)phosphide affords the 2,5-dihydro-1-phosphonia-2-stanna-5-boratole 8 which is fluxional with respect to the coordinative P-B bond. In a similar way, the reaction of 1 with lithium diphenylphosphide gives the analogous derivative 9 which however, posseses a strong coordinative P-B bond. Compound 9 is also accessible from the reaction of the 1,5-dihydro-1,1,4,5,5-pentaethyl-2,2,3-trimethyl-1-azonia-2-stanna-5-boratole 2 with diphenylphosphane. All products were characterised by 1 H, 11 B, 13 C, 14 N, 29 Si, 31 P and 119 Sn NMR data. Several absolute signs of coupling constants were determined by appropriate 2D heteronuclear shift correlations. NMR data of 8 were compared with those of Me 3 SnP(SiMe 3 ) 2 , determined here for the first time. INTRODUCTION1,1-Organoboration of 1-alkynyltin compounds [1,2] has opened the route to many useful heterocyclic compounds or to their precursors. Thus, (E)-2-(chlorodimethylstannyl)-3-diethylboryl-pent-2-ene 1 [3] and 1,1,4,5,5-pentaethyl-2,2,3-trimethyl-1-azonia-2-stanna-5-boratole 2 [4] are readily available (Scheme 1), and the presence of numerous reactive sites is promising for further useful transformations of these compounds [5],

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“…(But‐3‐yn‐1‐yloxy)trimethylsilane 25 (3ac): Prepared from but‐3‐yn‐1‐ol ( 2c ; 7.8 μL, 0.10 mmol, 1.0 equiv.) according to GP1, 84 % yield (NMR, Table 2).…”

Section: Methodsmentioning

confidence: 99%

Prediction of Flow Patterns of Rotating Inclined Reactors by Using a Modified Permeability Approach

et al. 2016

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A new inclined rotating tubular fixed bed reactor was recently suggested for process intensification of heterogeneous catalytic multiphase reactions. Favorable operating conditions can be achieved by operating the reactor in a wetting intermittency mode by periodic catalyst immersion in a stratified gas‐liquid flow. This flow pattern adjustment, which requires the careful selection of reactor inclination and rotation, eventually enhances the reaction rate. To predict the flow patterns by means of computational fluid dynamics, a 3D model based on the relative permeability approach was developed, in which gas and liquid phases flow concurrently downwards through the inclined rotating tubular fixed bed reactor. The model can clearly predict the four evolving patterns, depending on the operating conditions. The model was capable of correctly predicting the hydrodynamics for aqueous liquid mixtures with varying viscosity and surface tension.

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Organoboration of 3-(Trinethylstannayal)-2-Propyny-1-Ethers

Cited by 18 publications

References 30 publications

Aminoethynyl‐silanes, ‐germanes and ‐stannanes: novel organometallic‐substituted enamines via 1,1‐organoboration

Aminoethynyl‐silanes, ‐germanes and ‐stannanes: novel organometallic‐substituted enamines via 1,1‐organoboration

Novel Organo-Substituted 2,5-Dihydro-1-Azoniaand -1-Phosphonia-2-Stanna-5-Boratoles

Prediction of Flow Patterns of Rotating Inclined Reactors by Using a Modified Permeability Approach

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