Carbenhomologe Verbindungen von Germanium, Zinn und Blei mit 2-substituiertenN-Pyrrolyl-Liganden

Hübler, Klaus; Hübler, Ute

doi:10.1002/(sici)1521-3749(200005)626:5<1224::aid-zaac1224>3.0.co;2-v

Cited by 8 publications

(5 citation statements)

References 9 publications

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“…The other known germylene complex with a pyrrole moiety is Ge(NC 4 H 3 COR) 2 (R = Me 2 N, Me, H). It contains a pyrrole derivative as a ligand and was obtained by reacting germylenediamide Ge[N(TMS) 2 ] 2 with the pyrrole-based ligand HNC 4 H 3 COR …”

Section: Results and Discussionmentioning

confidence: 99%

“…Calcd for C 19 H 27 GeN 3 (M = 370.08): C,61.66;H,7.35;N,11.35. Found: C,61.42;H,7.18;N,11.05. 1 H NMR (300 MHz, CDCl 3 ): δ 0.89 (d, 3 J HH = 6.6 Hz, 6H, CH(CH 3 ) 2 ), 0.97 (d, 3 J HH = 6.3 Hz, 6H, CH(CH 3 ) 2 ), 2.05−2.19 (m, 2H, CH(CH 3 ) 2 ), 3.22 (dd, J HH = 13.8, 8.1 Hz, 2H, CH 2 ), 3.37 (dd, J HH = 13.8, 6.0 Hz, 2H, CH 2 ), 6.17 (s, 2H, CH pyrrole ), 6.59 (s, 2H, CH pyrrole ), 6.52−6.68 (m, 3H, CH ring ), 7.14−7.21 (m, 2H, CH ring ).…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

“…It contains a pyrrole derivative as a ligand and was obtained by reacting germylenediamide Ge[N(TMS) 2 ] 2 with the pyrrole-based ligand HNC 4 H 3 COR. 11 To test the feasibility of substitution reactions on a heterocycle-functionalized germylene, compound 2 was reacted with various reagents with acidic protons. Eventually, it was identified that such reactivity on compound 2 is possible cleanly with thio-and selenophenol.…”

Section: ■ Introductionmentioning

confidence: 99%

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Synthesis and Reactivity ofN-Aminotroponiminatogermylenepyrrole and Its Derivatives

et al. 2013

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Through the reaction of the aminotroponiminatogermylene monochloride complex [(Bu i 2ATI)GeCl] (1) with sodium pyrrolide, the stable N-germylene pyrrole complex [(Bu i 2ATI)GeNC4H4] (2) has been isolated. The reaction of compound 2 with thiophenol and selenophenol afforded the first germylene thio- and selenophenoxide complexes [(Bu i 2ATI)GeSPh] (3) and [(Bu i 2ATI)GeSePh] (4) through the substitution of the pyrrole moiety (NC4H4) with an EPh moiety (E = S (3), Se (4)), respectively. Interestingly, the chalcogenide derivatives of compound 2, such as the N-germathioacylpyrrole complex [(Bu i 2ATI)Ge(S)NC4H4] (5) and N-germaselenoacylpyrrole complex [(Bu i 2ATI)Ge(Se)NC4H4] (6), also underwent the aforementioned substitution reaction with thiophenol and selenophenol, resulting in the first examples of germa thioester complexes ([(Bu i 2ATI)Ge(S)SPh] (7) and [(Bu i 2ATI)Ge(Se)SPh] (8)) and germa selenoester complexes ([(Bu i 2ATI)Ge(S)SePh] (9) and [(Bu i 2ATI)Ge(Se)SePh] (10)), respectively. All the novel germanium compounds 3–10 have been unequivocally characterized through multinuclear NMR spectroscopy along with the germylene complex 2. Further, compounds 3–5 and 7–10 were characterized through single-crystal X-ray diffraction studies. The GeII–S and GeII–Se bond lengths in compounds 3 and 4 are 2.367(1) and 2.511(1) Å, respectively. The average GeIV–S and GeIV–Se bond lengths in germa thioester (7 and 8) and germa selenoester (9 and 10) complexes are 2.241(1) and 2.362(1) Å, respectively.

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Section: Results and Discussionmentioning

confidence: 99%

Section: ■ Experimental Sectionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

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Synthesis and Reactivity ofN-Aminotroponiminatogermylenepyrrole and Its Derivatives

et al. 2013

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“…Pyrrole-2-carboxaldehyde forms a stable coordination complex ( A ) in conjunction with acetylacetone and copper(II), nickel(II), palladium(II), or platinum(II) . Pyrrole-2-acyl species and imino derivatives therefrom also form complexes with various metals or coordination centers ( B , C , D , E , and F ). We began our search for suitable metal complexes of 1-acyldipyrromethanes on the basis of the known complexes of 2-acylpyrroles.…”

Section: Introductionmentioning

confidence: 99%

Boron-Complexation Strategy for Use with 1-Acyldipyrromethanes

et al. 2004

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Abstract1-Acyldipyrromethanes are important precursors in rational syntheses of diverse porphyrinic compounds. 1-Acyldipyrromethanes are difficult to purify, typically streaking upon chromatography and giving amorphous powders upon attempted crystallization. A solution to this problem has been achieved by reacting the 1-acyldipyrromethane with a dialkylboron triflate (e.g., Bu 2 B-OTf or 9-BBN-OTf) to give the corresponding B,B-dialkyl-B-(1-acyldipyrromethane)boron(III) complex. The reaction is selective for a 1-acyldipyrromethane in the presence of a dipyrromethane. The 1-acyldipyrromethane-boron complexes are stable to routine handling, are soluble in common organic solvents, crystallize readily, are hydrophobic, and chromatograph without streaking. The 1-acyldipyrromethane can be liberated in high yield from the boron complex upon treatment with 1-pentanol. Alternatively, the 1-acyldipyrromethane-boron complex can be used in the formation of a trans-A 2 B 2 -porphyrin. In summary, the boron-complexation strategy has broad scope and greatly facilitates the isolation of 1-acyldipyrromethanes.

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“…The coordination polyhedron is most often a tetrahedron; in the structure of C 32 H 16 N 8 Si (PHPRSI; Aldoshin et al, 1980), however, the CP is a square. Besides, the Ge atoms have the bisphenoid coordination polyhedra in the structures of five compounds ( Table 5 of the supplementary material), namely C 14 H 18 GeN 4 O 2 (MELNUM; Hubler & Hubler, 2000), C 13 H 19 GeN 2 ÁCF 3 SO 3 (UFUHOS; Ayers & Dias, 2002), C 4 H 8 O 2 ÁCl 2 Ge (DIOXGC01; Marsh, 1997;or DIOXGC02;Denk et al, 1998) and C 4 H 8 O 2 ÁBr 2 Ge (FITLUP; Gar et al, 1987). There are also five Si and ten Ge compounds with CN = 5, where the CP is a square pyramid (A atom is situated in the base) or a trigonal bipyramid.…”

Section: Refcodementioning

confidence: 99%

Special features of intermolecular bondingA...D(A= Si, Ge andD= nucleophile) in crystal structures

Вологжанина

Korlyukov

Antipin

2008

Acta Crystallogr Sect B

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An investigation of the crystal structures of 3346 silicon- and 718 germanium-containing compounds was carried out with a geometrical-topological analysis. The descriptors of inter- and intramolecular contacts A...D are given. Information on the descriptors of T-A...D (where T = leaving group) interactions in terms of a stereoatomic model of crystal structures was described as being helpful in modelling S(N)2 reactions. It was established that the formation of multiple intermolecular contacts in crystal structures is unfavorable. The dependence of the descriptors of intermolecular contacts T-A...D was studied as a function of the nature of T (leaving group in substitution reactions) and D (nucleophile atom or group of atoms) groups, and the coordination number of an A atom. The constancy of the T-A and A...D bond-order sum in crystal structures was demonstrated.

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Carbenhomologe Verbindungen von Germanium, Zinn und Blei mit 2-substituiertenN-Pyrrolyl-Liganden

Cited by 8 publications

References 9 publications

Synthesis and Reactivity ofN-Aminotroponiminatogermylenepyrrole and Its Derivatives

Synthesis and Reactivity ofN-Aminotroponiminatogermylenepyrrole and Its Derivatives

Boron-Complexation Strategy for Use with 1-Acyldipyrromethanes

Special features of intermolecular bondingA...D(A= Si, Ge andD= nucleophile) in crystal structures

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