¹H NMR SPECTROSCOPY IN THE STUDY OF THE THREE-DIMENSIONAL STRUCTURE OF 7-ALKOXYALKYL-3-THIA-7-AZABICYCLO[3.3.1]NONAN-9-ONES AND SOME OF THEIR DERIVATIVES

Abstract

1H NMR spectroscopy was used to establish that 7-alkoxyalkyl-3-thia-7-azabicyclo[3.3.1]nonan-9-ones and their decarbonylated derivatives in deuterochloroform solution exist in the double chair conformation. The predominantly formed secondary alcohols isomers have preferred double chair conformation with the hydroxyl group equatorial relative to the plane of the piperidine ring. On the other hand, the epimeric alcohols have predominant boat-chair conformation; the piperidine ring takes the boat form due to intramolecular hydrogen  bonding between the unshared electron pair of the nitrogen atom and hydroxyl group proton.

How to Cite
Klepikova, S. G.; Yu, V. K.; Fomicheva, E. E.; Mukhasheva, R. D.; Praliev, K. D.; Berlin, K. D.  Chem. Heterocycl. Compd. 2008, 44, 1398. [Khim. Geterotsikl. Soedin. 2008, 1716.]

For this article in the English edition see DOI 10.1007/s10593-009-0188-8