Undecenyl resorc[4]arene in the chair conformation as preorganized synthon for olefin metathesis (Articolo in rivista)

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  • Undecenyl resorc[4]arene in the chair conformation as preorganized synthon for olefin metathesis (Articolo in rivista) (literal)
Anno
  • 2013-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1039/c3ra42943a (literal)
Alternative label
  • F. Ghirga, I. D'Acquarica, G.D. Monache, S. Toscano, L. Mannina, A.P. Sobolev, F. Ugozzoli, D. Crocco, R. Antiochia, B. Botta (2013)
    Undecenyl resorc[4]arene in the chair conformation as preorganized synthon for olefin metathesis
    in RSC advances; RSC Publishing, Cambridge (Regno Unito)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • F. Ghirga, I. D'Acquarica, G.D. Monache, S. Toscano, L. Mannina, A.P. Sobolev, F. Ugozzoli, D. Crocco, R. Antiochia, B. Botta (literal)
Pagina inizio
  • 17567 (literal)
Pagina fine
  • 17576 (literal)
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  • http://www.scopus.com/inward/record.url?eid=2-s2.0-84883895446&partnerID=q2rCbXpz (literal)
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  • 3 (literal)
Rivista
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroFascicolo
  • 38 (literal)
Note
  • Scopu (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • Dipartimento di Chimica e Tecnologie Del Farmaco, Sapienza Università di Roma, P. le Aldo Moro 5, Roma 00185, Italy; Laboratorio di Risonanza Magnetica Annalaura Segre, Istituto di Metodologie Chimiche CNR Area della Ricerca di Roma, Via Salaria km 29.300, Monterotondo 00015, Italy; Dipartimento di Chimica Generale, Università di Parma Parco, Area delle Scienze 17/a, Parma 43100, Italy (literal)
Titolo
  • Undecenyl resorc[4]arene in the chair conformation as preorganized synthon for olefin metathesis (literal)
Abstract
  • Tetramerization of (E)-2,4-dimethoxycinnamic acid v-undecenyl ester with ethereal BF3 gave three stereoisomers 1a, 1b, and 1c, which were assigned as the chair, cone, and 1,2-alternate conformations, respectively. The chair conformation of 1a was confirmed by X-ray diffraction analysis, which also showed a peculiar self-assembly behavior in the crystal lattice, forming intercalated hydrophilic and hydrophobic layers (6-7 Å thickness) as a consequence of strong CH-p interactions. Undecenyl resorc[4]arene 1a, which featured the simplest pattern of substituents, was submitted to olefin metathesis using the second generation Grubbs complex as the catalyst. Depending on the reaction conditions, different products were isolated: a bicyclic alkene 2a (46%), a linear dimer 3a (5%), and a cross-linked homopolymer P1a (44%) (literal)
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