Uncommon Aqueous Media for Nitrilimine Cycloadditions. I. Synthetic and Mechanistic Aspects in the Formation of 1-Aryl-5-substituted-4,5-dihydropyrazoles (Articolo in rivista)

Type
Label
  • Uncommon Aqueous Media for Nitrilimine Cycloadditions. I. Synthetic and Mechanistic Aspects in the Formation of 1-Aryl-5-substituted-4,5-dihydropyrazoles (Articolo in rivista) (literal)
Anno
  • 2002-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1039/b205063c (literal)
Alternative label
  • G. Molteni, A. Ponti, M. Orlandi (2002)
    Uncommon Aqueous Media for Nitrilimine Cycloadditions. I. Synthetic and Mechanistic Aspects in the Formation of 1-Aryl-5-substituted-4,5-dihydropyrazoles
    in New journal of chemistry (1987)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • G. Molteni, A. Ponti, M. Orlandi (literal)
Pagina inizio
  • 1340 (literal)
Pagina fine
  • 1345 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
  • 26 (literal)
Rivista
Note
  • ISI Web of Science (WOS) (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • Universita` di Milano, Dipartimento di Chimica Organica e Industriale, via Golgi 19, 20133, Milano, Italy. E-mail: giorgio.molteni@unimi.it; Fax: 02-50314139; Tel: 02-50314141 Consiglio Nazionale delle Ricerche, Istituto di Scienze e Tecnologie Molecolari, via Golgi 19, 20133, Milano, Italy Universita` di Milano-Bicocca, Dipartimento di Scienze dell'Ambiente e del Territorio, Piazza della Scienza 1, 20126, Milano, Italy (literal)
Titolo
  • Uncommon Aqueous Media for Nitrilimine Cycloadditions. I. Synthetic and Mechanistic Aspects in the Formation of 1-Aryl-5-substituted-4,5-dihydropyrazoles (literal)
Abstract
  • A number of 1-aryl-5-substituted-4,5-dihydropyrazoles 4 have been synthesised by 1,3-dipolar cycloaddition of variously substituted nitrilimines 2 onto the appropriate alkenyl dipolarophiles 3 in aqueous media and in the presence of a surfactant. Under these conditions, uncommon for the large majority of [3+2] cycloadditions, the electronic features of both the cycloaddends strongly dictate the reaction outcome. Clean and fast cycloadditions were observed between electron-rich nitrilimines and electron-poor dipolarophiles, while the reversal of the electronic features of the reactants gave poor results. Changes in surfactant concentration leads to some novel mechanistic insights. (literal)
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