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Hauptgruppenelementanaloga Von Carbenen, Olefinen Und Kleinen Ringen

M. Driess, H. Grützmacher
Published 1996 · Chemistry

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Lange galten Methylen (:CH2), Ethylen (H2C=CH2) und Cyclopropan [(CH2)3] als Verbindungen, deren hohere Homologe oder Analoga nicht synthetisiert werden konnen. Eine Konsequenz der experimentellen Miserfolge war zum Beispiel die immer noch haufig angefuhrte, vor mehr als zwanzig Jahren aufgestellte Doppelbindungsregel, die zwar Verbindungen mit Mehrfachbindungen nicht ihre Existenz abspricht, diese aber als kinetisch instabil ausweist. Diese Auslegung der Doppelbindungsregel ist lange uberholt, und die verbesserten experimentellen und quantenchemischen Methoden erlauben nun die Herstellung bzw. die Charakterisierung von Methylen-, Ethylen- und Cyclopropan-analogen Hauptgruppenelementverbindungen, die bei Raumtemperatur in Losung und im Festkorper stabil sind. Im vorliegenden Aufsatz werden aktuelle Entwicklungen bei der Synthese dieser Verbindungen geschildert und die Konzepte skizziert, die durch systematische Studien entwickelt werden konnten. Dabei wird auf eine detaillierte Beschreibung der komplexen Reaktivitat der einzelnen Verbindungsklassen verzichtet und versucht, grundlegende Prinzipien herauszuheben. Mit diesen lassen sich Strukturen, Reaktivitaten und Eigenschaften zumindest grob vorhersagen. Und in diesen unterscheiden sich formel- und sogar strukturanaloge Verbindungen mit Elementen aus den hoheren Perioden deutlich von denen ihrer leichteren Homologen. Wahrend zum Beispiel jeder Chemiker mit der planaren, D2h -symmetrischen Struktur von H2C=CH2 als einzig „sinnvollem” Isomer bestens vertraut ist, darf er fur Sn2 H4 funf Isomere annehmen, die sich nur wenig in ihrer Energie unterscheiden. Wahrend fur die cis/trans-Isomerie von Olefinen nur die Rotation um die C-C-Doppelbindung in Frage kommt, sind fur Disilenderivate R1 RSi=SiR1 R drei Mechanismen moglich. Cyclopropane galten im vergangenen Jahrhundert ebenfalls als nicht herstellbar und waren Anstos fur Baeyers Spannungstheorie. Untersuchungen an den viel spater entdeckten kleinen Siliciumcyclen zeigten, das diese Theorie fur diese Ringe viel besser gilt. Langsam wird durch das gesammelte Datenmaterial deutlich, das die einst als Vorbilder herangezogenen Kohlenstoffverbindungen die wahrhaft „exotischen” Verbindungen sind. Regeln mit breiter Gultigkeit lassen sich daher besser durch Studien an Verbindungen mit Hauptgruppenelementen aus den hoheren Perioden ableiten.
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Insight into the Electron Density Distribution in an O,N‐Heterocyclic Stannylene by High‐Resolution X‐ray Diffraction Analysis
M. Chegerev (2019)
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Aluminum(I)/Boron(III) Redox Reactions.
A. Hofmann (2019)
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A Redox-Active Bis(ferrocenyl)germylene and Its Reactivity.
Y. Suzuki (2018)
10.1002/chem.201804684
A Stabilized Bisphosphanylsilylene and Its Heavier Congeners.
D. Kargin (2018)
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N-Functionalized Ferrocenes: Subvalent Group XIV Element Chlorides and tert-Butyllithium-Induced C-C Bond Cleavage under Mild Conditions.
Bastian Nayyar (2018)
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Synthesis and Reactivity of Donor-Stabilized Bis(pentafluoroethyl)stannylene [Sn(C2 F5 )2 (D)n ] (D=THF, DMAP, PMe3 , [Sn(C2 F5 )3 ]- ).
J. Klösener (2018)
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N‐funktionalisierte Ferrocene. Niedervalente Elementchloride der XIV. Gruppe und eine durch tert‐Butyllithium induzierte C‐C‐Bindungsspaltung unter milden Bedingungen
Bastian Nayyar (2018)
10.1002/chem.201801292
Pentafluoroethylated Compounds of Silicon, Germanium and Tin.
Markus Wiesemann (2018)
10.1002/EJIC.201700177
A Computational Study on the Stability of Oxaphosphirane Rings towards Closed‐Shell Valence Isomerization
A. Ferao (2017)
10.1002/chem.201700494
Ligand-Supported E3 Clusters (E=Si-Sn).
Sudip Pan (2017)
10.1016/B978-0-12-814213-4.00001-0
X-Ray Crystallography of Organosilicon Compounds (Electron Density and Chemical Bonding in Organosilicon Compounds)
Benedikt Niepoetter (2017)
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Intramolecular Tetrylene Lewis Adducts: Synthesis and Reactivity.
J. Schneider (2016)
10.1002/anie.201511956
A Stable Heterocyclic Amino(phosphanylidene-σ(4)-phosphorane) Germylene.
Natalia del Rio (2016)
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[Ge2](4-) Dumbbells with Very Short Ge-Ge Distances in the Zintl Phase Li3NaGe2: A Solid-State Equivalent to Molecular O2.
L. M. Scherf (2016)
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Nickel-triad complexes of a side-on coordinating distannene.
Christian P Sindlinger (2015)
10.1002/ANGE.201411025
Distannenkomplexe der Nickeltriade
Christian P Sindlinger (2015)
10.1002/chem.201406486
Chemistry of stannylene-based Lewis pairs: dynamic tin coordination switching between donor and acceptor character.
K. M. Krebs (2015)
10.1002/ANGE.201310455
K4[PbSe4]⋅en⋅NH3 – eine nicht‐oxidische, Halogenid‐freie anorganische Blei(IV)‐Verbindung
G. Thiele (2014)
10.1039/c4cs00073k
New bonding modes of carbon and heavier group 14 atoms Si-Pb.
G. Frenking (2014)
10.1002/anie.201308525
From disilene (Si=Si) to phosphasilene (Si=P) and phosphacumulene (P=C=N).
Philipp Willmes (2014)
10.1002/ANGE.201308525
Von Disilen (SiSi) über Phosphasilen (SiP) zum Phosphakumulen (PCN)
Philipp Willmes (2014)
10.1002/chem.201402626
A theoretical investigation of photochemical reactions of an isolable silylene with benzene.
M. Su (2014)
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Dative Bindungen bei Hauptgruppenelementverbindungen: ein Plädoyer für mehr Pfeile
G. Frenking (2014)
10.1002/anie.201310455
K(4)[PbSe(4)]⋅en⋅NH(3) : a non-oxide, non-halide inorganic lead(IV) compound.
G. Thiele (2014)
10.1002/anie.201311022
Dative bonds in main-group compounds: a case for more arrows!
G. Frenking (2014)
10.1002/ZAAC.201300473
Structures and Bonding Situation of the Allyl Systems and Cyclic Isomers [H2E–E(H)–EH2]–,·,+ (E = C, Si, Ge, Sn) †‡
José A. Gámez (2013)
10.1002/anie.201301485
Critical comments on "One molecule, two atoms, three views, four bonds?".
G. Frenking (2013)
10.1002/ANGE.201206767
η2‐Koordinierendes Distannen – ein neuartiger Nickel(0)‐Komplex
J. Henning (2012)
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