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Struktur und Mechanismus bei Fragmentierungsreaktionen 1. Teil. Die stereoisomeren 10‐Chlor‐decahydro‐isochinoline. Fragmentierungsreaktionen, 23. Mitteilung
Author(s) -
Geisel M.,
Grob C. A.,
Wohl R. A.
Publication year - 1969
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.19690520804
Subject(s) - chemistry , carbonium ion , heterolysis , fragmentation (computing) , stereochemistry , medicinal chemistry , isoquinoline , ion , organic chemistry , catalysis , computer science , operating system
cis ‐10‐Chloro‐N‐methyl‐decahydro‐isoquinoline ( 5 ) and its trans ‐isomer 6 undergo heterolytic fragmentation in 80% ethanol by different mechanisms. As predictable on stereo‐chemical grounds the cis ‐isomer 5 reacts by the accelerated synchronous mechanism, the trans ‐isomer 6 , however, by the two‐step carbonium ion mechanism. Synchronous fragmentation therefore dominates over the two‐step process even when the latter would lead to a relatively stable tertiary carbonium ion. In both cases the more highly substituted and thermochemically more stable olefinic fragment 8 is formed.