Spiroheterocycles from reaction of nitrones with methylene-gamma-butyrolactones and some of their rearrangements.
Cycloaddition of nitrones 1 with methylene-gamma-butyrolactones 2, 3 and 4 afforded spiroadducts 5, 6 and 7 with high selectivity. Mixtures of diastereoisomers were usually obtained, whose structures were established by 1H and 13C NMR spectroscopies or X-ray crystallography. Treatment of spiroadducts in acidic and alkaline media led to different, unexpected and novel rearrangements.
Roussel
Christophe
C
Laboratoire de Chimie des Matériaux et Interfaces, UFR Sciences et Techniques, 16 Route de Gray, F-25030 Besancon, France.
Fihi
Rachid
R
Ciamala
Kabula
K
Vebrel
Joël
J
Zair
Touria
T
Riche
Claude
C