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Fragmentierung von α‐Aminoketoximen. V. Teil. (2‐Chinuclidinyl)‐phenyl‐ketoxim. Zur Gültigkeit der B REDT schen Regel bei energiereichen Zwischenstufen Fragmentierungsreaktionen, 18. Mitteilung
Author(s) -
Grob C. A.,
Sieber A.
Publication year - 1967
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.19670500839
Subject(s) - chemistry , benzonitrile , medicinal chemistry , stereochemistry
The reaction of (2‐quinuclidinyl) phenyl ketoxime tosylate ( 1 ) in aqueous ethanol or tetrahydrofuran yields 10 to 20% of benzonitrile and 4‐piperidyl‐acetaldehyde ( 6 ), the tautomer of 2‐quinuclidinol ( 5 ), besides N‐(2‐quinuclidinyl)‐benzamide ( 4 ). In phenol some 2‐phenoxyquinuclidin ( 21 ) and benzonitrile are obtained besides phenyl N‐(2‐quinuclidinyl)‐benzimidate ( 20 ). Furthermore, the α‐aminoketoximetosylate 1 reacts 2 to 4 times as fast as the homomorphous (bicyclo[2.2.2]‐2‐octyl) phenyl ketoxime tosylate ( 7 ). By contrast the latter untergoes quantitative Beckmann rearrangement to the amide 12 .