A Ring-Fusion/Ring-Fission Mechanism for the Metathesis Reaction of Macrocyclic Formaldehyde Acetals (Articolo in rivista)

Type
Label
  • A Ring-Fusion/Ring-Fission Mechanism for the Metathesis Reaction of Macrocyclic Formaldehyde Acetals (Articolo in rivista) (literal)
Anno
  • 2006-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1002/chem.200600983 (literal)
Alternative label
  • Cacciapaglia R.; Di Stefano S.; Mandolini L. (2006)
    A Ring-Fusion/Ring-Fission Mechanism for the Metathesis Reaction of Macrocyclic Formaldehyde Acetals
    in Chemistry - A European Journal
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Cacciapaglia R.; Di Stefano S.; Mandolini L. (literal)
Pagina inizio
  • 8566 (literal)
Pagina fine
  • 8570 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
  • 12 (literal)
Rivista
Note
  • Scopu (literal)
  • ISI Web of Science (WOS) (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • Dipartimento di Chimica e IMC-CNR Sezione Meccanismi di Reazione Università La Sapienza, Roma (literal)
Titolo
  • A Ring-Fusion/Ring-Fission Mechanism for the Metathesis Reaction of Macrocyclic Formaldehyde Acetals (literal)
Abstract
  • Important insight has been obtained into the mechanism of the reversible acid-catalysed transacetalation of cyclophane formaldehyde acetals (formals) Ci in CDCl3, at 25 °C. The order of appearance of the lowest oligomers in the early stages of the equilibration reaction is fully consistent with ring-fusion/ring-fission processes in which oxonium ion intermediates undergo SN2 reactions, according to an acid-catalysed bimolecular (A2) mechanism. The alternative acid-catalysed monomolecular (A1) reaction path, based on \"back-biting\" processes of carbenium ions generated by SN1- type cleavage of oxonium ion intermediates, predicts sequences that are in marked contrast with experimental findings. (literal)
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