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Durch Umlagerung induzierte Fragmentierung von 4‐Tosyloxymethyl‐chinuclidin und vergleichende Solvolyse von 1‐Tosyloxymethyl‐bicyclo[2,2,2]octan und Neopentyltosylat Fragmentierungsreaktionen, 3. Mitteilung
Author(s) -
Grob C. A.,
Hoegerle R. M.,
Ohta M.
Publication year - 1962
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.19620450613
Subject(s) - chemistry , solvolysis , carbonium ion , quinuclidine , bicyclic molecule , medicinal chemistry , fragmentation (computing) , stereochemistry , organic chemistry , hydrolysis , ion , computer science , operating system
A fragmentation reaction can be induced by generating a γ‐amino‐carbonium ion through a Wagner‐Meerwein rearrangement of a δ‐amino‐ p ‐toluenesulfonic ester. Thus solvolysis of 4‐tosyloxymethyl‐quinuclidine (9a) in aqueous ethanol yields the 4‐methylene‐1‐aza‐cycloheptanes (20a) and (20b).