1,4-Additions of tricyclic 1,4-diphosphinines – a novel system to study σ-bond activation and π–π dispersion interactions

Abhishek Koner; Zsolt Kelemen; Gregor Schnakenburg; László Nyulászi; Rainer Streubel

doi:10.1039/c7cc09349g

1,4-Additions of tricyclic 1,4-diphosphinines – a novel system to study σ-bond activation and π–π dispersion interactions

Chemical Communications ◽

10.1039/c7cc09349g ◽

2018 ◽

Vol 54 (10) ◽

pp. 1182-1184 ◽

Cited By ~ 8

Author(s):

Abhishek Koner ◽

Zsolt Kelemen ◽

Gregor Schnakenburg ◽

László Nyulászi ◽

Rainer Streubel

Keyword(s):

Bond Activation ◽

Thermal Conditions ◽

Cycloaddition Reactions ◽

Dispersion Interactions

The reactivity of the aromatic π-system in 1,4-diphosphinineIwas explored towards [4+2]-cycloaddition reactions along with activation of organo dichalcogenides under thermal conditions.

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Carbon−Carbon Bond Activation by Electrophilic Complexes of Cobalt: Anomalous [3 + 2 + 2] Allyl/Alkyne Cycloaddition Reactions and [5 + 2] Cyclopentenyl/Alkyne Insertion−Ring Expansion Reactions

Journal of the American Chemical Society ◽

10.1021/ja992598k ◽

1999 ◽

Vol 121 (45) ◽

pp. 10640-10641 ◽

Cited By ~ 34

Author(s):

Trevor L. Dzwiniel ◽

Nola Etkin ◽

Jeffrey M. Stryker

Keyword(s):

Bond Activation ◽

Ring Expansion ◽

Cycloaddition Reactions ◽

Carbon Bond ◽

Carbon Carbon Bond ◽

Alkyne Insertion

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Generation of Oxyallyl Cations by Reduction of α,α′-Diiodoketones Under Sonochemical or Thermal Conditions: Improved Methodology for the [4C(4π;)+3C(2π;)] Cycloaddition Reactions

Synthetic Communications ◽

10.1081/scc-120015712 ◽

2003 ◽

Vol 33 (2) ◽

pp. 265-279 ◽

Cited By ~ 17

Author(s):

Angel M. Montaña ◽

Pedro M. Grima

Keyword(s):

Thermal Conditions ◽

Cycloaddition Reactions ◽

Oxyallyl Cations

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New methodology for the [4+3] cycloaddition reactions: generation of oxyallyl cations from α,α′-diiodoketones under sonochemical or thermal conditions

Tetrahedron Letters ◽

10.1016/s0040-4039(01)01671-9 ◽

2001 ◽

Vol 42 (44) ◽

pp. 7809-7813 ◽

Cited By ~ 25

Author(s):

Angel M Montaña ◽

Pedro M Grima

Keyword(s):

Thermal Conditions ◽

Cycloaddition Reactions ◽

Oxyallyl Cations

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A Cationic Imido Complex of Permethyltantalocene: H2and Carbon−Hydrogen Bond Activation, [2 + 2] Cycloaddition Reactions, and an Unusual Reaction with Carbon Dioxide That Affords Coordinated Isocyanate

Organometallics ◽

10.1021/om970815p ◽

1998 ◽

Vol 17 (4) ◽

pp. 718-725 ◽

Cited By ~ 54

Author(s):

Robert E. Blake, ◽

David M. Antonelli ◽

Larry M. Henling ◽

William P. Schaefer ◽

Kenneth I. Hardcastle ◽

...

Keyword(s):

Carbon Dioxide ◽

Hydrogen Bond ◽

Bond Activation ◽

Unusual Reaction ◽

Cycloaddition Reactions ◽

Carbon Hydrogen Bond Activation

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Studies on chemo- and diastereo-selectivity of the Diels–Alder reactions of sulfinyltoluquinones with cyclopentadiene

Canadian Journal of Chemistry ◽

10.1139/v09-070 ◽

2009 ◽

Vol 87 (8) ◽

pp. 1135-1143 ◽

Cited By ~ 1

Author(s):

Andrea L. F. de Sousa ◽

José E. P. Cardoso Filho ◽

Blanka Wladislaw ◽

Liliana Marzorati ◽

Claudio Di Vitta

Keyword(s):

Thermal Conditions ◽

Alder Reaction ◽

Diels Alder ◽

Cycloaddition Reactions ◽

Double Bonds ◽

Diels Alder Reaction

Sulfinyltoluquinones (2a–2c) were submitted to thermal or catalyzed [4+2] cycloaddition reactions with cyclopentadiene. For p-tolylsulfinyltoluquinones (2b) and (2c), almost complete C2–C3-chemo- and unlike-diastereoselectivity was achieved by catalysis with ZnBr2, yielding adducts 6. Under thermal conditions, Diels–Alder reaction took place at the C5–C6 double bonds of quinones 2a–2c, generating mixtures of diastereoisomeric like- and unlike-adducts 4.

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Reactivity of the uranium(iv) carbene complex [U(BIPMTMS)(Cl)(μ-Cl)2Li(THF)2] (BIPMTMS= {C(PPh2NSiMe3)2}) towards carbonyl and heteroallene substrates: metallo-Wittig, adduct formation, C–F bond activation, and [2 + 2]-cycloaddition reactions

Dalton Transactions ◽

10.1039/c4dt00909f ◽

2014 ◽

Vol 43 (38) ◽

pp. 14275-14283 ◽

Cited By ~ 27

Author(s):

Oliver J. Cooper ◽

David P. Mills ◽

William Lewis ◽

Alexander J. Blake ◽

Stephen T. Liddle

Keyword(s):

Bond Activation ◽

Adduct Formation ◽

Cycloaddition Reactions ◽

Carbene Complex

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C–H Bond Activation ofMethane with Gaseous [(CH3)Pt(L)]+ Complexes (L = Pyridine, Bipyridine, and Phenanthroline)

Zeitschrift für Naturforschung B ◽

10.1515/znb-2007-0302 ◽

2007 ◽

Vol 62 (3) ◽

pp. 309-313 ◽

Cited By ~ 26

Author(s):

Burkhard Butschke ◽

Maria Schlangen ◽

Helmut Schwarz ◽

Detlef Schröder

Keyword(s):

Experimental Data ◽

Detailed Analysis ◽

Electrospray Ionization ◽

Kinetic Modeling ◽

Bond Activation ◽

Oxidative Addition ◽

Thermal Conditions ◽

Nitrogen Ligand ◽

Insight Into

Electrospray ionization of solutions of dimethyl(1,5-cyclooctadiene)platinum(II) in methanol with traces of nitrogen-containing ligands L provides gaseous complexes of the type [(CH3)Pt(L)]+ with L = pyridine (py), 2,2′-bipyridine (bipy), and 1,10-phenanthroline (phen). These [(CH3)Pt(L)]+ cations are capable of activating the C-H bond in methane as shown by H/D exchange when using CD4 as a neutral reactant. Most reactive is the complex [(CH3)Pt(py)]+ bearing a monodentate nitrogen ligand. The cationic complexes [(CH3)Pt(bipy)]+ and [(CH3)Pt(phen)]+ also bring about activation of methane, though at a lower rate, whereas the bipyridine complex [(CH3)Pt(py)2]+ does not react with methane at thermal conditions. A detailed analysis of the experimental data by means of kinetic modeling provides insight into the underlying mechanistic steps, but a distinction whether the reaction occurs as σ bond metathesis or via an oxidative addition cannot be made on the basis of the experimental data available.

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