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

Geisel M. | Zendy; Grob C. A. | Zendy; Wohl R. A. | Zendy

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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.

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