Synthetic Exploitation of the Ring-Opening of 3,4-Dinitrothiophene. Access to 1,4-Disubstituted 2,3-Dinitro-1,3-butadienes and 2,3-Butanedione Dioximes (Articolo in rivista)

Type
Label
  • Synthetic Exploitation of the Ring-Opening of 3,4-Dinitrothiophene. Access to 1,4-Disubstituted 2,3-Dinitro-1,3-butadienes and 2,3-Butanedione Dioximes (Articolo in rivista) (literal)
Anno
  • 1992-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1016/S0040-4020(01)80449-X (literal)
Alternative label
  • Dell'Erba C.; Mele A.; Novi M.; Petrillo G.; Stagnaro P. (1992)
    Synthetic Exploitation of the Ring-Opening of 3,4-Dinitrothiophene. Access to 1,4-Disubstituted 2,3-Dinitro-1,3-butadienes and 2,3-Butanedione Dioximes
    in Tetrahedron (Oxf., Print); Pergamon Press, Oxford (Regno Unito)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Dell'Erba C.; Mele A.; Novi M.; Petrillo G.; Stagnaro P. (literal)
Pagina inizio
  • 4407 (literal)
Pagina fine
  • 4418 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#url
  • http://ac.els-cdn.com/S004040200180449X/1-s2.0-S004040200180449X-main.pdf?_tid=3f7422de-ff85-11e2-89b2-00000aab0f27&acdnat=1375896033_c115463cb2361ecae4205bb7ee22ce10 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
  • 48 (literal)
Rivista
Note
  • ISI Web of Science (WOS) (literal)
  • copu (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • Dell'Erba C.; Mele A.; Novi M.; Petrillo G. Università di Genova Stagnaro P. Università di Genova (attualmente CNR-ISMAC Genova) (literal)
Titolo
  • Synthetic Exploitation of the Ring-Opening of 3,4-Dinitrothiophene. Access to 1,4-Disubstituted 2,3-Dinitro-1,3-butadienes and 2,3-Butanedione Dioximes (literal)
Abstract
  • The optimized ring-opening reaction of 3,4-dinitrothiophene 1 with either primary or secondary amines leads to 1,4-bis(alkylamino)- and 1,4-bis(arylamino)- 2 or 1,4-bis(dialkylamino)-2,3-dinitro-1,3-butadienes 3 in satisfactory to excellent yields. While compounds 2 in solution appear to be mixtures of (Z,Z), (Z,E) and (E,E) stereoisomers, whose composition is influenced by the nature of the solvent, compounds 3 appear as single (E,E) isomers. The reaction of 3 with various organometals in THF represents a novel access to unknown (E,E)-1,4-dialkyl- and (E,E)-1,4-diaryl-2,3-dinitro-1,3-butadienes 4. Finally, Pb-reduction of the two nitrovinylic functionalities of 4 effectively leads to the corresponding symmetrically 1,4-disubstituted 2,3-butanedione dioximes 5. (literal)
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