Fragmentierung von α‐Aminoketoximen. III. Teil Mono‐ und bicyclische Verbindungen. Fragmentierungs‐Reaktionen. 6 Mitteilung

The only observable reaction of the p‐toluene sulfonates of six mono‐ and bicyclic α‐aminoketoximes (2d–7d) is fragmentation to carbimonium salts (8–13). The fragmentation product of 1‐keto‐octahydropyrrocolineoxime‐tosylate (6d), viz. the carbimonium salt (12), undergoes spontaneous ring closure to 2‐oxo‐1‐azaquinolizidine (26). The intermediate (12) in this fragmentation‐recombination reaction can be intercepted by cyanide ion, yielding β(2‐cyano‐piperid‐l‐yl)‐propionnitrile (29 a).