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[3+1]-Cyclisierungen zu Tetraboraporphyrinogenen / [3+1]-Cycloadditions with Formation of Tetraboraporphyrinogenes

  • Thomas K¨ohler , Hans Pritzkow and Walter Siebert EMAIL logo
Published/Copyright: June 2, 2014
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Zeitschrift für Naturforschung B
From the journal Zeitschrift für Naturforschung B Volume 57 Issue 10

Abstract

2,5-Bis(chloro-2,2,6,6-tetramethylpiperidinoboryl)thiophene (1) and 2,5-bis(chloro-diisopropylaminoboryl) pyrrol (4) react with two equivalents of 2-lithiothiophenide to yield the corresponding 2,5-diborylheteroarenes (2,5) in which two boryl groups connect three heteroarenes. After lithiation of the terminal thiophenes of both compounds in 5,5'-position their reactions with the diborylthiophene 1 as well as with diborylpyrrol 4, lead to tetraboraporphyrinogenes (3, 6), the latter being the first tetraboratetraazaporphyrinogene. By silicon / boron exchange of 1-trimethylsilylimidazol with the 2,5-diborylpyrrol 4 the 2,5-bis(imidazolyldiisopropylamino- boryl)pyrrol 7 is formed, which reacts with BH3 and BEt3 to give the N-borane adducts of 7. The spectroscopic data and four X-ray structure analyses are reported.

Keywords : Porphyrinogenes; Lithiation; Di(2-heteroaryl)boranes
Received: 2002-5-8
Published Online: 2014-6-2
Published in Print: 2002-10-1

© 1946 – 2014: Verlag der Zeitschrift für Naturforschung

Articles in the same Issue

  1. Nitridsulfidhalogenide der leichten Lanthanide vom Typ M6N3S4X (M = La - Nd; X = Cl, Br) mit ausgeordneten Sulfid- und Halogenid-Lagen / Nitride Sulfide Halides of the Light Lanthanides with the Formula Type M6N3S4X (M = La - Nd; X = Cl, Br) with Ordered Sulfide and Halide Positions
  2. Bis(triphenylphosphoranylidene)ammonium Dicyanoaurate(I)
  3. Die neuen Oxobismutate(III) Cs6Bi4O9, K9Bi5O13 und A2Bi4O7 (A = Rb, Cs) / The New Oxobismutates(III) Cs6Bi4O9, K9Bi5O13 and A2Bi4O7 (A = Rb, Cs)
  4. [3+1]-Cyclisierungen zu Tetraboraporphyrinogenen / [3+1]-Cycloadditions with Formation of Tetraboraporphyrinogenes
  5. Mercury Cyanamide / Carbodiimide Networks: Synthesis and Crystal Structures of Hg2(NCN)Cl2 and Hg3(NCN)2Cl2
  6. Self-Assembly of Organo-Sulfur, Selenium and Tellurium Compounds via π-π-Stacking and Hydrogen Bonding Interactions
  7. DFT Calculations of the Structures of Various Isomers (cis/trans) of [(CH3)(PH3)M-NH2-CH2-C(O)-O] and [(Cl)(PH3)M-NH2-CH2-C(O)-O] Complexes with M = Ni, Pd and Pt
  8. Eine einfache Synthese von 1,3-Dihydro-1,3-diborapentafulven-Derivaten / A Convenient Synthesis of 1,3-Dihydro-1,3-diborapentafulvene Derivatives
  9. Crystal Structure and Magnetic Properties of (2,2'-Dipyridyl)-(2-acetylphenolato)copper(II) Perchlorate
  10. Synthesis, Crystal Structures and Investigations on the Thermal Properties of New CuBr(2-Ethylpyrazine) Coordination Polymers
  11. Novel Non-Symmetric Nickel-Diimine Complexes for the Homopolymerization of Ethene: Control of Branching by Catalyst Design
  12. The First 6,8-Cycloeudesmane Sesquiterpene from a Marine Organism: The Red Seaweed Laurencia microcladia from the Baia di Calenzana, Elba Island
  13. Polysulfonylamine, CLIX [1]. Eine Vielfalt supramolekularer Synthone in zwei Molekülkomplexen von Di(4-halogenbenzolsulfonyl)aminen mit Sauerstoffbasen / Polysulfonylamines, CLIX [1]. A Variety of Supramolecular Synthons in Two Molecular Complexes of Di(4-halobenzenesulfonyl)amines with Oxygen Bases
  14. A Simple Conversion of 2'-Benzyloxyflavanone to Pterocarpan
  15. Synthesis of Rigid Cyclopropanoid Nucleoside Analogues
  16. Manganese(II), Iron(II), Cobalt(II) and Nickel(II) Complexes of Methanesulfonic Acid Hydrazide. Crystal Structure of trans-Dichlorotetrakis(methanesulfonic Acid Hydrazide-N2)cobalt(II) and trans-Dichlorotetrakis(methanesulfonic Acid Hydrazide-N2)nickel(II)
  17. Synthesis of a Dinuclear μ-(η2-Thioaldehyde)zirconocene Cation Complex
  18. Crystal Structure of trans- [ReCl2(dppp)2]Cl · ½H2O (dppp = 1,3-bis(diphenylphosphino)propane)
https://doi.org/10.1515/znb-2002-1004
Keywords for this article
Porphyrinogenes; Lithiation; Di(2-heteroaryl)boranes

Articles in the same Issue

  1. Nitridsulfidhalogenide der leichten Lanthanide vom Typ M6N3S4X (M = La - Nd; X = Cl, Br) mit ausgeordneten Sulfid- und Halogenid-Lagen / Nitride Sulfide Halides of the Light Lanthanides with the Formula Type M6N3S4X (M = La - Nd; X = Cl, Br) with Ordered Sulfide and Halide Positions
  2. Bis(triphenylphosphoranylidene)ammonium Dicyanoaurate(I)
  3. Die neuen Oxobismutate(III) Cs6Bi4O9, K9Bi5O13 und A2Bi4O7 (A = Rb, Cs) / The New Oxobismutates(III) Cs6Bi4O9, K9Bi5O13 and A2Bi4O7 (A = Rb, Cs)
  4. [3+1]-Cyclisierungen zu Tetraboraporphyrinogenen / [3+1]-Cycloadditions with Formation of Tetraboraporphyrinogenes
  5. Mercury Cyanamide / Carbodiimide Networks: Synthesis and Crystal Structures of Hg2(NCN)Cl2 and Hg3(NCN)2Cl2
  6. Self-Assembly of Organo-Sulfur, Selenium and Tellurium Compounds via π-π-Stacking and Hydrogen Bonding Interactions
  7. DFT Calculations of the Structures of Various Isomers (cis/trans) of [(CH3)(PH3)M-NH2-CH2-C(O)-O] and [(Cl)(PH3)M-NH2-CH2-C(O)-O] Complexes with M = Ni, Pd and Pt
  8. Eine einfache Synthese von 1,3-Dihydro-1,3-diborapentafulven-Derivaten / A Convenient Synthesis of 1,3-Dihydro-1,3-diborapentafulvene Derivatives
  9. Crystal Structure and Magnetic Properties of (2,2'-Dipyridyl)-(2-acetylphenolato)copper(II) Perchlorate
  10. Synthesis, Crystal Structures and Investigations on the Thermal Properties of New CuBr(2-Ethylpyrazine) Coordination Polymers
  11. Novel Non-Symmetric Nickel-Diimine Complexes for the Homopolymerization of Ethene: Control of Branching by Catalyst Design
  12. The First 6,8-Cycloeudesmane Sesquiterpene from a Marine Organism: The Red Seaweed Laurencia microcladia from the Baia di Calenzana, Elba Island
  13. Polysulfonylamine, CLIX [1]. Eine Vielfalt supramolekularer Synthone in zwei Molekülkomplexen von Di(4-halogenbenzolsulfonyl)aminen mit Sauerstoffbasen / Polysulfonylamines, CLIX [1]. A Variety of Supramolecular Synthons in Two Molecular Complexes of Di(4-halobenzenesulfonyl)amines with Oxygen Bases
  14. A Simple Conversion of 2'-Benzyloxyflavanone to Pterocarpan
  15. Synthesis of Rigid Cyclopropanoid Nucleoside Analogues
  16. Manganese(II), Iron(II), Cobalt(II) and Nickel(II) Complexes of Methanesulfonic Acid Hydrazide. Crystal Structure of trans-Dichlorotetrakis(methanesulfonic Acid Hydrazide-N2)cobalt(II) and trans-Dichlorotetrakis(methanesulfonic Acid Hydrazide-N2)nickel(II)
  17. Synthesis of a Dinuclear μ-(η2-Thioaldehyde)zirconocene Cation Complex
  18. Crystal Structure of trans- [ReCl2(dppp)2]Cl · ½H2O (dppp = 1,3-bis(diphenylphosphino)propane)
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