Struktur und Mechanismus bei Fragmentierungsreaktionen 1. Teil. Die stereoisomeren 10‐Chlor‐decahydro‐isochinoline. Fragmentierungsreaktionen, 23. Mitteilung

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Abstract
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.

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