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Cascade Reaction of Camphor-Derived Diynes with Transition Metal Compounds

  • M. Fernanda N. N. Carvalho EMAIL logo , Armando J. L. Pombeiro , Gabriele Wagner , Bjørn Pedersen and Rudolf Herrmann
Published/Copyright: June 2, 2014
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Zeitschrift für Naturforschung B
From the journal Zeitschrift für Naturforschung B Volume 54 Issue 6

Platinum(II) catalyzes the isomerization of camphor sulfonamide diynes in a cascade reaction involving annulation of a five-membered ring to the camphor skeleton, ring-enlargement by C-C bond cleavage, reduction of sulfur(VI) to sulfur(IV), and oxidation of a hydroxy group to a ketone. The reactions of the diynes with other transition metal compounds were also studied. Copper, gold and rhenium give final products similar to those obtained with simple Brønsted acids or halogens, mainly by annulation o f a five-membered ring to the camphor moiety, accompanied by reduction of a sulfonamide to a sulfinamide group, but lacking the ring-enlargement step. Palladium(II) occupies an intermediate position as both types o f products are obtained. The reaction mechanism and intermediates are discussed

Keywords: Camphor Diyne; Ring Enlargement; Transition Metals; Catalysis; Alkyne
Received: 1999-3-18
Published Online: 2014-6-2
Published in Print: 1999-6-1

© 1946 – 2014: Verlag der Zeitschrift für Naturforschung

Articles in the same Issue

  1. Decomposition of Ethoxyethynyl(trimethyl)tin - Studied by 119Sn and 13C NMR Spectroscopy
  2. New Stannides CaTSn2 (T = Rh, Pd, Ir) and Ca2Pt3Sn5 - Synthesis, Structure and Chemical Bonding
  3. Synthesis and Structural Study of the Thermochromic Compounds Bis(2-amino-4-oxo-6-methylpyrimidinium) Tetrachlorocuprate(II) and Bis(2-amino-4-chloro-6-methylpyrimidinium) Hexachlorodicuprate(II)
  4. Cascade Reaction of Camphor-Derived Diynes with Transition Metal Compounds
  5. Metallkomplexe mit biologisch wichtigen Liganden, CXIX [1]. Ein tetraedrischer Zink-Komplex (L-terf-Leucin)2ZnCl2 mit Carboxylat-koordiniertem L-terf-Leucin in der / Zwitterform Metal Complexes of Biologically Important Ligands, CXIX [1]. A Tetrahedral Zinc Complex (L-terf-Leucine)2ZnCl2 of Carboxylate Coordinated L-terr-Leucine in the Zwitterionic Form
  6. Untersuchungen zum chemischen Transport intermetallischer Phasen, I: GeTe, SnTe, PbTe / Investigations on the Chemical Transport of Intermetallic Phases, I: GeTe, SnTe, PbTe
  7. Kristallstruktur des „supramolekularen“ Komplexes [K(Benzo-18-krone-6)][Zn(CN)3]*H2O mit einem polymeren kettenförmigen Tricyanozincat-Anion / Crystal Structure of the “Supramolecular” Complex [K(benzo-18-crown-6)][Zn(CN)3] •H2O with a Polymeric Tricyano Zincate Anion with Chain Structure
  8. 1.2-Verzweigte Carbosiloxan-Dendrimere mit Hauptgruppenelementund Übergangsmetall-modifizierten Oberflächen / 1.2-Branched Carbosiloxane-Dendrimers with Main-Group Element and Transition-Metal Modified Surfaces
  9. Darstellung und Kristallstruktur von Triammonium-trisulfimid (NH4)3(NSO2)3 / Preparation and Crystal Structure of Triammonium-trisulfimid (NH4)3(NSO2)3
  10. Synthese und Röntgenstrukturanalyse der ersten terf-Butylcalix[4]arensalze mit einem Phosphonium-Kation / Synthesis and X-Ray Structure Analysis of the First rm-Butylcalix[4]arene Salts with a Phosphonium Cation
  11. Kristallstrukturen und Normalkoordinatenanalyse von trans-(n-Bu4N)2 [ReCl4IX], X = NCS, NCSe / Crystal Structures and Normal Coordinate Analyses of trans-(n-Bu4 N)2[ReCl4 IX], X = NCS, NCSe
  12. Darstellung, 11B-NMR- und Schwingungsspektren von c/s-Monoethylmononitrotetrahydro- c/050-hexaborat(2-) sowie Kristallstruktur von cis (Ph4As)2[B6H4(C2H5)(NO2)] / Synthesis, 11B NMR and Vibrational Spectra of cis-Monoethylmononitrotetrahydroc-closo-hexaborate(2-) and Crystal Structure of cis-(Ph4As)2[B6 H4 (C2H5 )(NO2)]
  13. Complexes of Group 12 Metals with 2-Acetylpyridine 4N-Dimethylthiosemicarbazone and with 2-Acetylpyridine-N-oxide 4N-Dimethylthiosemicarbazone: Synthesis, Structure and Antifungal Activity
  14. Synthesis of Pyrimidine, Thiazolopyrimidine, Pyrimidotriazine and Triazolopyrimidine Derivatives and their Biological Evaluation
  15. SbCI3, BiCl3 and Na+ Complexes of Maleonitrile-Dithiacrown Ethers: Synthesis, Crystal Structures and DEP-MS Experiments
  16. Zatatriol: A New Aromatic Constituent from Zataria multiflora
  17. A Facile Synthesis of Naphthyl-Quinolyl Ethanes and Chromenyl-Quinolyl Ethanes
  18. Microwave-Assisted Oxidation of Alcohols Using Wet Alumina Supported Ammonium Chlorochromate in Solventless System
  19. Die Kristallstruktur von [(THF)LiCl]n / The Crystal Structure of [(THF)LiCl]n
  20. Fixation o f Neutral Molecules in the Binding Cavity of Nonplanar Porphyrins - A Third Dodecaphenylporphyrin Modification with NH -Solvent Hydrogen Bonding
https://doi.org/10.1515/znb-1999-0604
Keywords for this article
Camphor Diyne; Ring Enlargement; Transition Metals; Catalysis; Alkyne

Articles in the same Issue

  1. Decomposition of Ethoxyethynyl(trimethyl)tin - Studied by 119Sn and 13C NMR Spectroscopy
  2. New Stannides CaTSn2 (T = Rh, Pd, Ir) and Ca2Pt3Sn5 - Synthesis, Structure and Chemical Bonding
  3. Synthesis and Structural Study of the Thermochromic Compounds Bis(2-amino-4-oxo-6-methylpyrimidinium) Tetrachlorocuprate(II) and Bis(2-amino-4-chloro-6-methylpyrimidinium) Hexachlorodicuprate(II)
  4. Cascade Reaction of Camphor-Derived Diynes with Transition Metal Compounds
  5. Metallkomplexe mit biologisch wichtigen Liganden, CXIX [1]. Ein tetraedrischer Zink-Komplex (L-terf-Leucin)2ZnCl2 mit Carboxylat-koordiniertem L-terf-Leucin in der / Zwitterform Metal Complexes of Biologically Important Ligands, CXIX [1]. A Tetrahedral Zinc Complex (L-terf-Leucine)2ZnCl2 of Carboxylate Coordinated L-terr-Leucine in the Zwitterionic Form
  6. Untersuchungen zum chemischen Transport intermetallischer Phasen, I: GeTe, SnTe, PbTe / Investigations on the Chemical Transport of Intermetallic Phases, I: GeTe, SnTe, PbTe
  7. Kristallstruktur des „supramolekularen“ Komplexes [K(Benzo-18-krone-6)][Zn(CN)3]*H2O mit einem polymeren kettenförmigen Tricyanozincat-Anion / Crystal Structure of the “Supramolecular” Complex [K(benzo-18-crown-6)][Zn(CN)3] •H2O with a Polymeric Tricyano Zincate Anion with Chain Structure
  8. 1.2-Verzweigte Carbosiloxan-Dendrimere mit Hauptgruppenelementund Übergangsmetall-modifizierten Oberflächen / 1.2-Branched Carbosiloxane-Dendrimers with Main-Group Element and Transition-Metal Modified Surfaces
  9. Darstellung und Kristallstruktur von Triammonium-trisulfimid (NH4)3(NSO2)3 / Preparation and Crystal Structure of Triammonium-trisulfimid (NH4)3(NSO2)3
  10. Synthese und Röntgenstrukturanalyse der ersten terf-Butylcalix[4]arensalze mit einem Phosphonium-Kation / Synthesis and X-Ray Structure Analysis of the First rm-Butylcalix[4]arene Salts with a Phosphonium Cation
  11. Kristallstrukturen und Normalkoordinatenanalyse von trans-(n-Bu4N)2 [ReCl4IX], X = NCS, NCSe / Crystal Structures and Normal Coordinate Analyses of trans-(n-Bu4 N)2[ReCl4 IX], X = NCS, NCSe
  12. Darstellung, 11B-NMR- und Schwingungsspektren von c/s-Monoethylmononitrotetrahydro- c/050-hexaborat(2-) sowie Kristallstruktur von cis (Ph4As)2[B6H4(C2H5)(NO2)] / Synthesis, 11B NMR and Vibrational Spectra of cis-Monoethylmononitrotetrahydroc-closo-hexaborate(2-) and Crystal Structure of cis-(Ph4As)2[B6 H4 (C2H5 )(NO2)]
  13. Complexes of Group 12 Metals with 2-Acetylpyridine 4N-Dimethylthiosemicarbazone and with 2-Acetylpyridine-N-oxide 4N-Dimethylthiosemicarbazone: Synthesis, Structure and Antifungal Activity
  14. Synthesis of Pyrimidine, Thiazolopyrimidine, Pyrimidotriazine and Triazolopyrimidine Derivatives and their Biological Evaluation
  15. SbCI3, BiCl3 and Na+ Complexes of Maleonitrile-Dithiacrown Ethers: Synthesis, Crystal Structures and DEP-MS Experiments
  16. Zatatriol: A New Aromatic Constituent from Zataria multiflora
  17. A Facile Synthesis of Naphthyl-Quinolyl Ethanes and Chromenyl-Quinolyl Ethanes
  18. Microwave-Assisted Oxidation of Alcohols Using Wet Alumina Supported Ammonium Chlorochromate in Solventless System
  19. Die Kristallstruktur von [(THF)LiCl]n / The Crystal Structure of [(THF)LiCl]n
  20. Fixation o f Neutral Molecules in the Binding Cavity of Nonplanar Porphyrins - A Third Dodecaphenylporphyrin Modification with NH -Solvent Hydrogen Bonding
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