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Tartaggia, Stefano; De Lucchi, Ottorino; Gambaro, Andrea; Zangrando, Roberta; Fabris, Fabrizio; Scarso, Alessandro

Chiral M3L2 Self‐Assembled Capsules through Metal Coordination of Enantiopure Ligating Benzocyclotrimers: NMR Spectroscopic and ESI Mass Spectrometric Investigation

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  • Medientyp: E-Artikel
  • Titel: Chiral M3L2 Self‐Assembled Capsules through Metal Coordination of Enantiopure Ligating Benzocyclotrimers: NMR Spectroscopic and ESI Mass Spectrometric Investigation
  • Beteiligte: Tartaggia, Stefano; De Lucchi, Ottorino; Gambaro, Andrea; Zangrando, Roberta; Fabris, Fabrizio; Scarso, Alessandro
  • Erschienen: Wiley, 2013
  • Erschienen in: Chemistry – A European Journal
  • Sprache: Englisch
  • DOI: 10.1002/chem.201203598
  • ISSN: 0947-6539; 1521-3765
  • Schlagwörter: General Chemistry ; Catalysis ; Organic Chemistry
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  • Beschreibung: <jats:title>Abstract</jats:title><jats:p>The synthesis of enantiopure (+)‐benzotricamphor <jats:italic>syn</jats:italic>‐<jats:bold>5</jats:bold>, an important chiral <jats:italic>C</jats:italic><jats:sub>3</jats:sub>‐symmetric rigid building block for supramolecular applications, was studied in detail to reduce the number of steps and to increase the diastereoselectivity and overall yield. The new synthetic procedure allowed larger amounts of <jats:italic>syn</jats:italic>‐<jats:bold>5</jats:bold> to be obtained and used for the preparation of new derivatives, such as the corresponding <jats:italic>tris</jats:italic>‐trifluoromethanesulfonate <jats:italic>syn</jats:italic>‐<jats:bold>12</jats:bold>, which was efficiently transformed into (+)‐benzotribornenetrinitrile <jats:italic>syn</jats:italic>‐<jats:bold>1</jats:bold> and (+)‐benzotribornenetris(ethynyl‐4‐pyridine) <jats:italic>syn</jats:italic>‐<jats:bold>2</jats:bold>. The previously reported (+)‐benzotricamphortrioxime <jats:italic>syn</jats:italic>‐<jats:bold>6</jats:bold> was transformed into tris‐nitrile <jats:italic>syn</jats:italic>‐<jats:bold>3</jats:bold> by Beckman reaction. Compounds <jats:italic>syn</jats:italic>‐<jats:bold>1</jats:bold>–<jats:bold>3</jats:bold> were employed as multidentate ligands for silver(I) and platinum(II) centres in apolar solvents. The linear coordination geometry of Ag<jats:sup>I</jats:sup> and square‐planar geometry of <jats:italic>cis</jats:italic>‐chelated Pt<jats:sup>II</jats:sup> in combination with the chiral tripodal ligands <jats:italic>syn</jats:italic>‐<jats:bold>1</jats:bold>–<jats:bold>3</jats:bold> led to the formation of chiral enantiopure capsules with M<jats:sub>3</jats:sub>L<jats:sub>2</jats:sub> stoichiometry, as confirmed by 2D NMR NOESY and DOSY experiments as well as ESI mass spectrometry.</jats:p>