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Neier, Reinhard

Nom
Neier, Reinhard
Affiliation principale
Fonction
Professeure ordinaire
Email
Reinhard.Neier@unine.ch
Identifiants
https://libra.unine.ch/handle/123456789/383
_
0000-0003-0890-1797

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  • Publication
    Métadonnées seulement
    Amino-Claisen rearrangements and Diels-Alder reactions of ketene N,O-acetals: Reactivity studies. On the way to a novel tandem process?
    (2000-1-12)
    Neuschutz, Klaus
    ;
    Simone, Jean-Mary
    ;
    Thyrann, Thomas
    ;
    Neier, Reinhard 
    We report the synthesis of N-benzyl-N-[(E)-buta-1,3-dienyl]propanamide (6) and its corresponding O-silyl-subitituted ketene N,O-acetal 7 and their Diels-Alder reaction. Propanamide G reacted smoothly, whereas the yield obtained from 7 was low, probably due to polymerization of the dienophile induced by electron transfer. The ketene N,O-acetals 27a-g were synthesized starting from the corresponding benzamides 25a-e (Scheme 9). The ketene N,O-acetals 27a-g showed increased stabilities and underwent amino-Claisen rearrangements under thermal conditions. Using catalysts, interesting side reactions leading either to the annulated systems, rac-35-37 or to a beta -lactam rac-34 were observed.
  • Publication
    Métadonnées seulement
    N,O- and N,S-ketene acetals as substrates for aza-Claisen rearrangement
    (1998)
    Neuschutz, Klaus
    ;
    Fernandez, Jimena
    ;
    Simone, Jean-Mary
    ;
    Neier, Reinhard 
    N,O-ketene acetals and N,S-ketene with a benzoyl group on the nitrogen are more stable than ketene acetals with a benzyl group on the nitrogen. These compds. undergo an aza-Claisen rearrangement. Due to high temps. and long reaction times needed, yields from N,O-ketene acetals are poor. N,S-ketene acetals are more stable than N,O-acetals, and temp. requirements to effect rearrangement are even higher. Catalysis, though attempted, could not be achieved. [on SciFinder(R)]