Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact: purchase@heterocycles.com

Price: ¥ 4,320 (Yen only)
Period: This Article can be accessed for 7 days.

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

Abstract

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.