SIN CHEONG WONG. Can. J. Chem. 57,1456 (1979.The tropane-3-spiro-5'-hydantoin (a isomer) obtained from tropinone by the BuchererBergs reaction has been shown by 13C nmr and X-ray diffraction studies to have the 4'-carbonyl group in the equatorial position; the isomer, obtained via the Strecker reaction, has this group axial. The results of these two reactions on cis-bicyclo[3.3.0]octan-3-one and on cis-3,4-dimethylcyclopentanone show, on the basis of the 'H nmr, 13C nmr, and X-ray diffraction studies of the products, a stereochemical course related to the preferred conformation of the cyclopentane rings.
Condensation of 2‐methylpyridinium salts with 1,2‐dicarbonyls in the presence of base, yielded 2,3‐disubstituted quinolizinium compounds. Results obtained with different pyridinium substrates are discussed.
l'alcoylation de la cyclohexanospirohydantoîne dans des conditions classiques et en transfert de phase conduit respectivement aux derivés N‐3‐substitués et aux derivés N‐1,N‐3‐disubstitués. l'application successive de ces méthodes a permis d'accéder facilement aux hydantoînes portant deux substituants différents. Les différents produits obtenus ont été etudiés par rmn du 13C. Cette méthode permet d'identifier les produits mono‐ et disubstitués ainsi que de déterminer la position du substituant.
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