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Paper | Regular issue | Vol 29, No. 6, 1989, pp.1191-1197
Published online, 1st January, 1970
DOI: 10.3987/COM-89-4955
Stereochemical Studies on 7- and 9-Substitutes 3-Azabicyclo[3.3.1]nonanes (3-ABNs)

Ramasubbu Jeyaraman* and Muthiah Manoharan*

*Department of Chemistry, Bharathidasan University, Tiruchirapalli-620024, India

Abstract

The conformations and configurations of some 3-azabicyclo[3.3.1]nonane (3-ABN) derivatives are discussed employing C-13 nmr spectral data. The monothioketal of 2,4-diphenyl-3-ABN-9-one exists in chair-chair conformation and has the oxygen axial to the piperidine ring. The product of Reformatsky reaction of the same ABN-9-one has the OH at C-9 to the side of the piperidine ring. The chair-boat conformation is assigned to one of the isomers of 7-methyl-2,4-diphenyl-3-ABN-9-one. The conformations of a few other ABNs are also discussed.