Chirality in the Absence of Rigid Stereogenic Elements: The Absolute Configuration of Residual Enantiomers of C3-Symmetric Propellers (Articolo in rivista)

Type
Label
  • Chirality in the Absence of Rigid Stereogenic Elements: The Absolute Configuration of Residual Enantiomers of C3-Symmetric Propellers (Articolo in rivista) (literal)
Anno
  • 2009-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1002/chem.200801489 (literal)
Alternative label
  • Benincori, T.; Marchesi, A.; Mussini, P.R.; Pilati, T.; Ponti, A.; Rizzo, S.; Sannicolo, F. (2009)
    Chirality in the Absence of Rigid Stereogenic Elements: The Absolute Configuration of Residual Enantiomers of C3-Symmetric Propellers
    in Chemistry - A European Journal
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Benincori, T.; Marchesi, A.; Mussini, P.R.; Pilati, T.; Ponti, A.; Rizzo, S.; Sannicolo, F. (literal)
Pagina inizio
  • 86 (literal)
Pagina fine
  • 93 (literal)
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  • 15 (literal)
Rivista
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  • DOI: 10.1002/chem.200801489 (literal)
Note
  • ISI Web of Science (WOS) (literal)
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  • [a] Prof. T. Benincori Dipartimento di Scienze Chimiche ed Ambientali Università dell'Insubria, via Valleggio 11 22100 Como (Italy) [b] Dr. A. Marchesi Laboratori Alchemia s.r.l., via S. Faustino 68 20134 Milano (Italy) [c] Prof. P. R. Mussini Dipartimento di Chimica Fisica ed Elettrochimica Universit? di Milano, via Venezian 21 20133 Milano (Italy) [d] Dr. T. Pilati, Dr. A. Ponti, Dr. S. Rizzo, Prof. F. Sannicol? Istituto di Scienze e Tecnologie Molecolari (ISTM) CNR via Golgi 19, 20133 Milano (Italy) E-mail: francesco.sannicolo@unimi.it [e] Prof. F. Sannicol? Dipartimento di Chimica Organica e Industriale C.I.MA.I.NA., Universit? di Milano, ISTM, CNR via Venezian 21, 20133 Milano (Italy) Fax: (+39) 02-5031-4139 Supporting information for (literal)
Titolo
  • Chirality in the Absence of Rigid Stereogenic Elements: The Absolute Configuration of Residual Enantiomers of C3-Symmetric Propellers (literal)
Abstract
  • Two new tris(aryl)phosphane oxides existing as configurationally stable residual enantiomers have been synthesised and their racemates resolved by semipreparative HPLC on a chiral stationary phase (CSP HPLC). One of them, recognised as a conglomerate, could be resolved by fractional crystallisation at a preparative scale level. In this case, the absolute configuration of the propeller-shaped molecule was determined by anomalous X-ray scattering. The problem of the correlative assignment of the absolute configuration to all known C-3-symmetric three-bladed propeller-shaped molecules existing as stable residual enantiomers is discussed. The configurational stability of the new chiral phosphane oxides and of the corresponding phosphanes was evaluated by CD signal decay kinetics and dynamic H-1 NMR spectroscopy. The racemisation barriers in phosphanes were found about 10 kcal mol(-1) lower than those found for the corresponding oxides, though geometry and inter-ring gearing would be very similar in the two series. Configurational stability of residual tris(aryl)phosphanes was found to be influenced by the electronic availability of the phosphorus centre, as evaluated by electrochemical CV experiments. (literal)
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