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Paper | Regular issue | Vol 24, No. 3, 1986, pp.719-732
Published online, 1st January, 1970
DOI: 10.3987/R-1986-03-0719
Synthesis and Structural Study of New Derivatives of 6,8-Diaryl-3-thia-7-azabicyclo[3.3.1]nonane Systems

Emilio F. Llama* and Gregorio G. Trigo

*Departamento de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad Complutense de Madrid, Ciudad Universitaria, 28040 Madrid, Spain


The synthesis and structural analysis of new derivatives of the 6,8-diaryil-3-thia-7-azabicyclo[3.3.1]nonane systems were studied. The high reactivity and stereoselectivity presented by this type of system demonstrates the rigid special arrangement acquired by this type of molecule. Nucleophilic attack on the carbonyl group of 6,8-diaryl-3-thia-7-azabicyclo[3.3.1]nonan-9-one (Grignard and Reformatsky reactions) exclusively produce β-isomers, unlike the Bucherer-Bergs reaction which produced a mixture of isomeric hydantoins. The percentage of isomers and the configuration at C-9 was determined by 1H-NMR spectroscopy. An IR study of solid state association in this type of molecule is presented.