Construction of bridged polycyclic systems via radical cyclizations. Uncovering of a novel carbocyclization-ring expansion sequence.
[reaction: see text]. While exploring the application of radical cyclizations to the construction of bridged polycyclic systems, we have discovered a novel tandem process consisting of an endo-cyclization of a vinyl radical onto a terminal alkene followed by a one-carbon ring expansion promoted by the resulting secondary radical.
Ramón Rodríguez
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Departamento de Química Orgánica y Unidad Asociada al CSIC, Universidad de Santiago de Compostela, 15782 Santiago de Compostela, Spain.
Castedo
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Mascareñas
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D001952:Bridged-Ring Compounds / Q000138:chemical synthesis*; D002625:Chemistry, Organic / Q000379:methods*; D003500:Cyclization; D005609:Free Radicals / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D008958:Models, Molecular; D011145:Polyvinyls / Q000737:chemistry; D013237:Stereoisomerism
D001952:Bridged-Ring Compounds; D005609:Free Radicals; D011145:Polyvinyls