Substitution effect on the cylization/fluorination reaction of N-dienes in superacid.
The novel cyclization/fluorination reaction of N-dienes in superacid was extended to substituted substrates. The influence of the substitution on superelectrophilic character of dicationic intermediates was shown and its dramatic effect on the synthesis of fluoropiperidines was studied. On the basis of new dicationic alpha-chloronium ammonium intermediates, starting from halogen-substituted dienes, high-valued fluorinated piperidines were synthesized.
Vardelle
Emilie
E
Université de Poitiers-UMR 6514-Laboratoire Synthèse et Réactivité des Substances Naturelles, 40, avenue du Recteur Pineau, F-86022 Poitiers Cedex, France.
Martin-Mingot
Agnès
A
Jouannetaud
Marie-Paule
MP
Bachmann
Christian
C
Marrot
Jérôme
J
Thibaudeau
Sébastien
S
D000475:Alkenes / Q000737:chemistry*; D000965:Antimony / Q000737:chemistry*; D003500:Cyclization; D005459:Fluorides / Q000737:chemistry*; D054879:Halogenation; D006219:Halogens / Q000737:chemistry; D006858:Hydrofluoric Acid / Q000737:chemistry*; D009584:Nitrogen / Q000737:chemistry*; D010880:Piperidines / Q000737:chemistry
D000475:Alkenes; D006219:Halogens; D010880:Piperidines; C529140:antimony pentafluoride; D000965:Antimony; D009584:Nitrogen; D005459:Fluorides; D006858:Hydrofluoric Acid