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Fragmentierung von α‐Aminoketoximen. III. Teil Mono‐ und bicyclische Verbindungen. Fragmentierungs‐Reaktionen. 6 Mitteilung
Author(s) -
Grob C. A.,
Fischer H. P.,
Link H.,
Renk E.
Publication year - 1963
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19630460415
Subject(s) - chemistry , fragmentation (computing) , bicyclic molecule , medicinal chemistry , toluene , cyanide ion , stereochemistry , ion , organic chemistry , computer science , operating system
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).