Summary:(E, Z)-l-Azacyclodeca-1, 6-diene 1-oxide (4) was generated by fragmentation of l- hydroxy-cis, cis-5-[(ptolylsulfonyl) oxy] decahydroquinoline (3a) under basic conditions. The nitrone 4 underwent in situ intramolecular cycloaddition to a l-aza-ll-oxatricyclo [5.3. 1.0 z~ 6] undecane (5)) and it could be trapped with styrene in an intermolecular dipolar cycloaddition to give 6. This concerted fragmentation reaction represents a useful nitrone synthesis.
