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The reactivity of 3,4‐dihydroisoquinoline N‐oxide (I) (with restricted relative orientation of the aromatic moiety and the nitrone function), which is known to be highly reactive in 1,3‐dipolar cycloadditions, is studied employing various ketenes.

By Anthony F. Gettins, David P. Stokes, Giles A. Taylor," and (in part) Christopher B. Judge, Department N-(Fluoren-9-ylidene)alkylamine N-oxides ( I ) react with diphenylketen to give spiro-oxazolidinones ( 2 ) and spiro-azetidinones (1 3). The adduct (2d) dissociates thermally to give the ylide ( 9 ) . The N-oxides (1) behave like normal nitrones in cycloaddition reactions with dipolarophiles.