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Étude Physico‐Chimique de Modèles D'Alcaloides Indoliques I. Considérations préliminaires concernant la structure d'analogues d'alcaloïdes indoliques et de dérivés du bicyclo [2, 2, 2] octane et du 1‐azabicyclo [2, 2, 2] octane (quinuclidine)

par Van Binst, Georges ;Nouls, Jean-Claude ;Martin, Ricardo
Référence Bulletin des Sociétés chimiques belges, 73, 3-4, page (226-240)
Publication Publié, 1964

Article révisé par les pairs

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Résumé :

In order to study the thermodynamic stability of the ethylidene side chain in a bridged bicyclic system, as it is found in certain alkaloids, we have prepared the following compounds: 2‐ethylidene bicyclo [2, 2, 2] octane, 2‐ethylbicyclo [2, 2, 2] oct‐2‐ene, 3‐ethyl‐1‐azabicyclo [2, 2, 2] oct‐2‐ene and 3‐ethylidene‐1‐azabicyclo [2, 2, 2] octane. From the results of the dehydratation of the 2‐ethylbicyclo [2, 2, 2] octan‐2‐ol and 3‐ethyl‐1‐azabicyclo [2, 2, 2] octan‐3‐ol, made in the same conditions as in acid catalysed isomerization, the following figures are obtained: ) series of bicyclo [2, 2, 2] octane: 30% of endocyclic alkene and 70% of semicyclic alkene; ) series of 1‐azabicyclo [2, 2, 2] octane: 25% of endocyclic alkene and 75% of semicyclic alkene. These figures show the peculiar stability of a semicyclic double bond with respect to an endocyclic double bond in 1, 4 bridged bicyclic compounds. Copyright © 1964 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim