Transient azomethine-ylides from a stable amino-carbene and an aldiminium salt.
Catalytic amounts of a protic reagent such as tert-butyl alcohol promote the isomerization of a stable amino-aryl-carbene into a transient azomethine ylide. Deprotonation of an alkyl-aldiminium salt also leads to a transient azomethine ylide, but labeling experiments rule out the transient formation of the corresponding amino-alkyl-carbene. The potential hypersurface between model amino-carbene, aziridine, and azomethine ylide is investigated.
Cattoën
Xavier
X
Laboratoire d'Hétérochimie Fondamentale et Appliquée du CNRS (UMR 5069), Université Paul Sabatier, 118, route de Narbonne, F-31062 Toulouse Cedex 04, France.
Solé
Stéphane
S
Pradel
Christian
C
Gornitzka
Heinz
H
Miqueu
Karinne
K
Bourissou
Didier
D
Bertrand
Guy
G