ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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.
Additional Material:
2 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19690520804
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