Spiroheterocycles from reaction of nitrones with methylene-gamma-butyrolactones and some of their rearrangements |
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| Authors: | Roussel Christophe Fihi Rachid Ciamala Kabula Vebrel Joël Zair Touria Riche Claude |
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| Institution: | Laboratoire de Chimie des Matériaux et Interfaces, UFR Sciences et Techniques, 16 Route de Gray, F-25030 Besancon, France. |
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| Abstract: | 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. |
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